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After 50 episodes with some of the top leaders in startups and tech, Annie Riley takes a moment to reflect and share her top five leadership takeaways that surfaced again and again throughout the latest season.
Annie also reflects on the current moment—from the rapid rise of AI to the growing need for authentic human connection—and why those realities have only strengthened her commitment to building a show that is honest, practical, and deeply human.
Plus, she shares what's next for Best Manager Ever as the team heads into a summer of experimentation, new formats, and fresh ways to support leaders navigating the messy middle of company building.
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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The stereotype of the hard-charging executive is hurting performance. Scott Lamb moved to NYC to pursue journalism, but ended up joining Buzzfeed when it was just five people and has been on the startup path ever since. In this episode, Scott sits down with Annie Riley to explore a different model for leadership– one rooted in curiosity, steadiness, psychological safety, and real human connection. They discuss what’s really behind vague feedback about “executive presence”, how management is a learnable craft, and how to have hard conversations that don’t FEEL bad.
Time Stamps:
00:00 — Why management matters
02:07 — Scott’s leadership style
04:08 — Joining BuzzFeed at five people
06:13 — Management is a skill
08:47 — The problem with “executive presence”
10:02 — Visibility vs. impact
13:21 — Directness over aggression
17:20 — Tough conversations done well
19:42 — Leading through layoffs
22:19 — Avoiding emotional dumping
24:56 — How to fire someone clearly
29:29 — The power of “say more”
37:22 — Listening and accountability
43:04 — Why humor matters at work
48:06 — Reps over perfection
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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The voice pushing you forward is also holding you back, and your inner critic is costing you more than you think. Annie Riley talks with clinical psychologist and self-compassion teacher Dr. Michael Klein to explore the psychology behind ambition, achievement, and the never-ending pursuit of "more." They discuss why success doesn't automatically lead to happiness, how striving and self-criticism can narrow creativity and reduce judgment. And they explore practical self compassion tools to help high-achieving leaders become more resilient, focused, creative, and effective.
Time Stamps:
00:00 – Introduction
01:00 – Why self-compassion matters for leaders
06:30 – Understanding the threat system
11:15 – The antidote to constant stress
13:00 – The striver's trap
18:00 – Why kindness doesn't kill ambition
20:15 – The self-compassion break
29:00 – Mindfulness, resistance, and suffering
33:00 – Responding instead of reacting
37:00 – Working with your inner critic
41:00 – Bringing compassion into the workplace
43:00 – Building a sustainable practice
49:00 – A better edge than self-criticism
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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JZ has built product teams at Airbnb, Webflow, Dropbox (and now Laurel), and in this episode she shares her honest leadership playbook and lessons learned. JZ covers why conviction is really about speed to signal, how to move fast without creating chaos, and why great leaders should share uncertainty instead of performing conviction. JZ also shares hot takes about 1:1 meetings, asking for help, and scrapping work that isn’t going in the right direction. This conversation between JZ and Annie Riley is packed with practical frameworks for managers and startup operators who want to move faster and build teams that thrive in ambiguity.
TimeStamps:
00:00 — Meet JZ
03:03 — The “fast-moving river” analogy
05:38 — Getting people to jump in
07:22 — Hiring for curiosity and urgency
10:11 — What “speed to signal” means
12:43 — Building through fast feedback
16:16 — The 3 leadership traps
20:41 — Operating at 120%
23:54 — Sharing unfinished work early
27:14 — Open sourcing strategy and workflows
31:34 — Knowing when to stop
34:16 — Graduating out of one-on-ones
36:23 — Asking for help effectively
40:23 — Trust, communication, and speed
43:41 — Ownership, introspection, and time
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This episode is sponsored by Blomma, the AI career coach built to help people grow with more clarity, accountability, and insight over time. Use code MANAGER for a free month and early access: https://www.blomma.com/
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Don’t let perfectionist fantasies kill progress. Annie Riley sits down with Anna Randall, Director of Enterprise Sales at Curri and former VP of Sales at TigerEye, Autodesk, and PlanGrid, to explore the power of “temporary permanent” thinking. They break down why the best teams prioritize momentum over precision, normalize imperfect solutions, and keep moving when the path changes. Plus: why the traditional “lone wolf” sales mentality is a bad thing, and the best leaders win as a pack.
Time Stamps:
00:00 Meet Anna Randall
02:16 Startup vs enterprise: autonomy, control, and team dynamics
04:38 Grit builds excellence: repetition over talent
06:23 Navigating early-stage chaos in real time
09:52 “Standing on the sun” + embracing uncertainty
10:24 “Temporary permanent”
13:31 The limits of grit:
16:21 The pack mentality: why lone wolves lose
21:07 Connecting team performance to the bigger “why”
23:19 Rethinking one-on-ones: making them actually valuable
27:38 Building trust through human connection
30:22 Saying the hard thing
33:29 Negotiation as trade-offs and “cards”
38:53 Managing expectations
43:35 Choosing the pack over self
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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Work is not like school– there are no right answers, and if you’re looking to be “right” then you will always fall behind. Annie Riley sits down with Silvia Oviedo Lopez, Founder & CEO of Blomma AI and former Canva and Pinterest leader, to unpack how the best leaders train curiosity, learn in real time, and see hard questions as a gift.
Time Stamps:
00:00 — Meet Silvia Oviedo Lopez
03:48 — How to Position Yourself for Growth
05:25 — Be Someone Who Brings Clarity
09:28 — Fast Learning Loops
10:44 — Pattern Matching vs. Fresh Thinking
12:34 — Curiosity Is a Muscle
16:16 — Coaching Without “Right vs. Wrong”
18:18 — Let Go and Keep Moving
27:05 — Scaling as a Leader
33:15 — Building Complementary Teams
36:57 — Leading People Smarter Than You
41:04 — What Are You Hearing From Your Team?
42:33 — Curiosity as a Leadership Superpower
43:16 — Flexibility in a Changing World
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App Store
Use code MANAGER for early access at blomma.com
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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Better questions create better teams. Annie Riley sits down with Maayan Roth, Head of Engineering at Crux Climate, to unpack the skill most managers overlook: asking questions that actually move things forward. Maayan shares how to use curiosity to uncover what’s really going on and guide conversations without controlling them. Plus: the traps new managers fall into, the difference between coaching and interrogating, and the simple question that turns hesitation into action.
TimeStamps:
00:00 – Meet Maayan Roth
02:53 – Startup leadership: building everything from scratch
05:27 – Why asking better questions is a leadership superpower
06:16 – Open vs. closed questions
08:28 – The “Socratic trap” and fake curiosity
10:09 – Letting go of having the answer
12:03 – Why leaders should speak last
14:17 – Go-to questions to unblock your team
18:58 – How to know if you’re asking the right questions
23:39 – Common traps: not listening, fake coaching, dead ends
31:23 – When coaching doesn’t work (and switching styles)
32:20 – What coaching actually means as a manager
39:31 – Growth should feel uncomfortable
43:46 – Hard lesson: stop doing everything so your team can step up
47:07 – There’s no “easy mode” in leadership + finding your people
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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Leadership is lonely. Most leaders don’t get enough support or positive feedback. And that includes our own boss too. Annie Riley and top executive coach Ed Batista break down why it’s so hard to empathize up— and how simple shifts like checking in or offering genuine positive feedback can change the dynamic, because sometimes the most powerful move is truly seeing the person behind the role.
Time Stamps:
00:00 Meet Ed Batista
02:36 Why empathizing up is so hard
03:48 The myth of the “invulnerable” leader
05:11 How to actually start empathizing up
06:45 Why your boss isn’t getting enough positive feedback
08:39 Empathizing up vs. managing up
09:56 Empathy does not mean agreement
12:03 What to do when your boss shuts you down
16:34 It’s probably not about you
20:07 Intent vs. impact
24:50 Leaders as shock absorbers
31:49 Pain is mandatory. Suffering is optional.
33:50 The danger of overvaluing feelings at work
39:07 Is the story you’re telling serving you?
41:52 Leadership is intuition, not a formula
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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You don’t become a great manager by regurgitating frameworks. Management is a craft and a skillset that gets built over time. Annie Riley sits down with Maura Church, VP of Product & Engineering at Two Chairs, to talk about how a manager’s mindset impacts team performance. From the “Smart Rats” theory to balancing tough feedback with real belief, Maura breaks down how to coach growth, build confidence, and unlock better results.
TimeStamps:
00:00 — Meet Maura Church
02:54 — Management is a craft, not a side job
04:49 — Why startups can’t afford bad management
07:14 — “No one is coming to save us”
10:09 — The trap of managing by checklist
13:07 — Giving feedback without making it personal
19:06 — “Smart Rats”: belief as a performance levers
25:13 — Turning “non-technical” skills into strengths
38:55 — Clear expectations make feedback easier
41:39 — Psychological safety is built, not assumed
45:10 — Rewriting the rules as your team evolves
47:15 — There’s no one “right” way to manage
Join us on Substack
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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Building a strong network is a skill. Annie Riley sits down with Whitnie Narcisse, former First Round Capital Partner, to unpack how she has built one of the best networks in Silicon Valley. Whitnie breaks down how to be memorable and build connections that last using her FACE framework (Factual, Authentic, Credible, and Engaging). Plus: why most networking advice falls flat, how to design rooms people want to be in, and the biggest networking mistake most people make.
Time Stamps:
00:00 – Whitnie's 3 biggest career inflection points
05:50 - How Whitnie got to First Round
06:50 – Agency in networking
09:30 – What actually gets a response
11:30 – Async networking and respecting people’s time
13:30 – Why most networking formats don’t work
15:30 – Building a high-value community and ecosystem
18:30 – The secret to great events
21:00 – How to create meaningful connections
23:30 – The FACE framework: how to be memorable
29:00 – The follow-up gap: why networking really starts after the handshake
31:00 – Generosity, authenticity, and playing the long game
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Connect with Whitnie Narcisse
Nominate Your Best Manager Ever
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“Polite silence” is a silent killer on teams. Annie Riley sits down with Dorothy Kilroy, Chief Commercial Officer at Oura Ring and former Airbnb to talk about how to invite productive disagreement while fostering psychological safety and how to give direct feedback without making it personal. Plus: the career-changing power of building your own “Boast Bitches”—a trusted circle that advocates for you and helps you grow.
TimeStamps:
00:38 – Meet Dorothy Kilroy
03:20 – Storytelling, mission-driven work, and bringing your full self
05:30 – The leadership shift: from having answers to building others
06:44 – Vulnerability at work: not therapy, but a signal of self-awareness
08:48 – Psychological safety + high standards
11:45 – “I believe in you”: the simplest, most powerful leadership tool
17:59 – Inviting disagreement: how to avoid false harmony on your team
21:54 – High standards without fear
26:00 – Reflection as a system
29:01 – Burnout, recovery, and building sustainable performance
32:40 – Feedback that drives growth
37:00 – “I” vs.“We”: balancing ownership and accountability
38:06 – Get yourself some “Boast Bitches”: building your personal board of directors
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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Speed beats perfection every time. Annie Riley dives in with Junan Pang, VP of Customer Success at Intercom, to unpack how he gives direct reports the context they need to act independently. He talks through why most leaders under-share, and how quick, imperfect updates unlock better decisions– without drowning the team in meetings or messages.
Timestamps:
00:00 Meet Junan Pang
01:58 Learning as a mindset
05:28 Taking intentional steps back
08:48 Growth through manager & IC zigzags
14:32 Building authentic, long-term relationships
18:08 Being in the problem
22:32 Fast, imperfect context sharing
31:35 Learning through osmosis
37:26 Feedback as a daily practice
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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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
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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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
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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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
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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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: [email protected]
Join us on Substack
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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
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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
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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: [email protected]
Join us on Substack
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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
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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 unlockIf you’re interested in sponsoring an episode of Best Manager Ever, reach out: [email protected]
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
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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 changeIf you’re interested in sponsoring an episode of Best Manager Ever, reach out: [email protected]
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
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