Lenny's Podcast: Product | Career | Growth

How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin

January 15, 2026

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  • The core goal of learning proper etiquette, according to Sam Lessin in this episode of Lenny's Podcast, is to develop the skill of showing up in any room with a low heart rate, projecting calm and abundance rather than transactional scarcity. 
  • In professional settings, etiquette matters significantly because it builds trust, which is vital when technology makes interactions less personal and when founders are asking for trust regarding data or business. 
  • Social interactions should be treated like a game of ping-pong, requiring a balance between asking questions and offering information, and gracefully knowing when to end a conversation to leave others wanting more. 
  • Subtlety is key when winding down conversations, aiming to let people feel respected and maintain plausible deniability about ending the interaction. 
  • Scheduling etiquette dictates that the less senior or less busy person should default to accommodating the other party's availability, and using scheduling tools like Calendly should be done respectfully with real options. 
  • In written communication (especially email), respect busy recipients by keeping messages short, to the point, avoiding emojis in formal contexts, and being mindful of the order of recipients (To vs. CC) as it signals importance. 

Segments

Why Etiquette Matters Now
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(00:04:52)
  • Key Takeaway: Etiquette is a vital skill for founders in 2025/2026 because as technology centralizes, building trust for partnerships and business requires understanding and mirroring expected social behaviors.
  • Summary: Etiquette is crucial for founders navigating a world where technology is no longer a sideshow but a major deal, demanding trust when asking people to partner or share data. The shallow truth is that teaching etiquette to Silicon Valley types is inherently funny, contrasting the long-held narrative that only product focus matters. Showing up with good etiquette and context leads to greater long-term success by facilitating better working relationships.
Low Heart Rate Mindset
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(00:07:02)
  • Key Takeaway: Etiquette is a skill for maintaining a low heart rate, which counters the scarcity mindset often felt at high-stakes events like a Kleiner Perkins party.
  • Summary: Showing up with a high heart rate and transactional energy, like an ’energizer bunny,’ scares people off and projects the wrong vibe. Founders should cultivate the self-confidence and calm of abundance, understanding that one interaction is part of a larger story, not the entire story. This mindset encourages giving more than taking and focusing on building relationships rather than collecting contacts.
Entering Rooms and Introductions
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(00:10:11)
  • Key Takeaway: To maintain a low heart rate upon arrival, be early to allow a buffer, and repeat a person’s name immediately upon introduction to signal genuine engagement.
  • Summary: Arriving early prevents rushing in flustered, which elevates the heart rate; if late, a simple apology suffices without making a big deal of it. A firm handshake is required, and repeating the name back (e.g., “Hey Lenny, it’s great to meet you”) shows effort to connect beyond just collecting a contact. If someone else is late, do not harp on it, as this creates a negative dynamic for the meeting.
Conversation Flow and Balance
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(00:16:25)
  • Key Takeaway: Effective conversations require inclusive engagement, treating the interaction as a ping-pong game where questions are returned with shared insights, avoiding an interrogation style.
  • Summary: When meeting people, especially in situations with power dynamics, be inclusive rather than monopolizing the time of a notable person. While asking questions is good, avoid making it feel like an inquisition where only information is extracted without exchange. The goal is to hit the ball back, ensuring a give-and-get flow so the interaction feels like a mutual exchange, not a monologue.
Leaving Them Wanting More
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(00:19:19)
  • Key Takeaway: The primary goal of social interaction is to leave the other party feeling the interaction was interesting enough to warrant a continuation or expansion, avoiding oversharing.
  • Summary: Do not give your entire spiel immediately; instead, aim to leave people wanting more, which is partially achieved by knowing when to excuse yourself gracefully. This abundance mindset recognizes that this interaction is not the only opportunity one will have. Overly aggressive pursuit of contact information immediately signals a scarcity mindset, which is counterproductive to relationship building.
Handling Famous People
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(00:21:29)
  • Key Takeaway: When meeting famous or highly successful individuals, avoid both sycophantic behavior and feigned ignorance, treating them as people while recognizing the context.
  • Summary: It is ridiculous to ask a well-known person who they are, but it is equally wrong to be overly effusive, such as claiming they are the most important person you have ever met. The best approach is grace, recognizing they are people, and maintaining the abundance mindset that this is not the only chance to interact. The ideal outcome is leaving them thinking you were a nice person worth talking to again.
Hygiene and Dress Code Basics
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(00:24:01)
  • Key Takeaway: Fragrance should be subtle enough that it is not noticeable in either direction (neither bad nor overpowering), and clothing fit is vastly more important than brand expense.
  • Summary: A person’s scent should not be memorable for anyone, regardless of gender, as there is no advantage to an overpowering presence. Dress one level up from the expected minimum, but prioritize a well-fitting $20 shirt over a misfitting $500 one. If unsure about the dress code for an event, it is confident and humble to simply ask beforehand.
Dining Etiquette: Ordering and Paying
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(00:33:45)
  • Key Takeaway: When dining out with others, especially potential partners, avoid ordering the most expensive items and always offer to pay first, even if you expect to be declined.
  • Summary: Do not order the most expensive thing on the menu or be overly stingy with the tip, as these actions signal insensitivity to cost, even if the other party can afford it. When invited out, always offer to pay for the meal; if declined (as expected with VCs), the gesture is what matters. If you are treating someone well-known, you must tip generously, matching the level of generosity they would exhibit.
Dining Etiquette: Table Manners
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(00:41:37)
  • Key Takeaway: Basic table manners, such as knowing the B&D trick for bread and drinks placement and keeping the knife blade pointed inward when resting it, should be executed subtly so they do not become memorable.
  • Summary: The B&D trick helps identify your bread plate (B) and drink placement (D) at a large table, preventing awkward hesitation. When resting a knife, the blade should point inward toward the plate to avoid accidentally striking a neighbor. The ultimate goal of etiquette is to be invisible; your napkin should be in your lap, and your table manners should not be the memorable part of the dinner.
Humor and Self-Deprecation
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(00:43:09)
  • Key Takeaway: Humor is a powerful tool that signals mastery of a social situation, but it must be tailored to the audience and used sparingly, with self-deprecation being the safest form.
  • Summary: Telling a joke that pushes slightly over the line demonstrates comfort in the space, but failing to get a laugh is a high-risk maneuver that should be avoided early on. Keep a ranked file of jokes to deploy appropriately, but remember that humor should not be the sole focus of your personality. Making fun of yourself is always safer than making fun of others, which requires a high degree of established familiarity.
Winding Down Conversations
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(00:48:14)
  • Key Takeaway: Subtlety is crucial when exiting conversations to ensure others feel respected and maintain plausible deniability about the interaction ending.
  • Summary: Recognize the moment a conversation is passing and respect the need to move on. A subtle technique is introducing a third party into the conversation, effectively giving the original person their next interaction partner. The goal is to execute these transitions with enough subtlety that everyone involved can save face.
Scheduling Etiquette and Calendly
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(00:49:23)
  • Key Takeaway: The default for scheduling should be accommodating the other party, especially when there is a power or busyness hierarchy, rather than defaulting to impersonal scheduling links like Calendly.
  • Summary: Sam Lessin expresses strong dislike for Calendly as a default, viewing it as disrespectful when used by the less senior party. If a scheduling link must be used, it must contain real availability options. When rescheduling, the initiator must be significantly more accommodating to the other person’s availability.
Respecting Support Staff
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(01:05:16)
  • Key Takeaway: Showing deep respect for Executive Assistants (EAs), Personal Assistants (PAs), and service staff is the number one way to avoid looking classless in business settings.
  • Summary: Always offer an extra gesture of respect to anyone assisting with logistics, such as saying thank you to an EA who scheduled a meeting. Simple acts like asking where to place a used coffee cup show respect for staff. Treating support staff as equals is vital for maintaining a positive professional image.
Communication and Email Etiquette
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(01:02:26)
  • Key Takeaway: Email communication should prioritize brevity, clarity, and acknowledgement, treating the recipient’s time as valuable by avoiding long monologues and overly familiar elements like emojis.
  • Summary: Assume the recipient is busy; get to the point quickly and proofread all messages. Emojis signal a high level of familiarity and can be ambiguous, making them risky in business communication compared to clear wording. The order of recipients in the ‘To’ and ‘CC’ fields carries subtle meaning about who the primary audience is.
Meeting Etiquette (In-Person/Virtual)
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(01:02:31)
  • Key Takeaway: In-person meetings require arriving 10-15 minutes early (but not too early) and initiating small talk as a necessary ‘handshake’ before diving into business.
  • Summary: Do not arrive so early that you impose on the host’s time; walk around the block if necessary. Small talk functions as the TCP/IP handshake, establishing a normal connection before shifting to business. For virtual meetings, keeping the camera on, dressing appropriately, and ensuring the background is tidy (e.g., closed closet doors) are essential.
Exiting and Follow-Up Etiquette
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(01:06:00)
  • Key Takeaway: Exiting interactions should be low-production, often favoring an ‘Irish goodbye’ in large groups, but always include standing up for handshakes and sending prompt follow-up thank you notes.
  • Summary: Stand up when shaking hands as a sign of awareness and respect, rather than remaining seated. Send thank you notes after meetings to express gratitude for the time invested. Avoid making a production of leaving; in large settings, a quiet disappearance is often preferable to lengthy goodbyes.
AI Corner Insights
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(01:09:28)
  • Key Takeaway: AI is best utilized as a powerful tool to supercharge existing, fundamentally sound businesses, rather than being the sole defining feature of a new startup.
  • Summary: Sam Lessin uses AI to power Letter Meme, an aggregator that turns newsletters into daily cartoons. He views using AI in a startup as essential infrastructure, similar to using the cloud in 2010. He is skeptical of companies branded purely as ‘AI companies’ due to high capital consumption and commoditization risks.
Contrarian Corner: AI Investing
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(01:11:17)
  • Key Takeaway: Seed venture capitalists investing in companies branded strictly as ‘AI companies’ are likely to lose significant money because these businesses are too capital-intensive for seed returns and lack clear long-term lock-in.
  • Summary: The current AI narrative is a desperate search for the next ‘Terra Nova’ (like the internet was), but AI is better suited as a propellant for existing business models. Disciplined seed investors should avoid companies whose primary value proposition is ‘we are AI’ due to high dilution from capital needs. Opportunity lies in businesses managing the cultural implications of AI, such as verification tests (Voigt-Kampff style).
Lightning Round Recommendations
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(01:16:27)
  • Key Takeaway: Key recommended reading includes ‘Lessons of History’ for its high intellectual return on a short investment, and ‘Landman’ is a recent enjoyable TV show, despite its tendency to create superficial industry expertise.
  • Summary: Recommended books include ‘The Ancient City,’ ‘Man’s Search for Meaning,’ and highly, ‘The Lessons of History’ by Will Durant. The TV show ‘Landman’ is noted as being watched by many tech investors who then mistakenly believe they understand the energy industry. Podcasting is most rewarding when done raw with friends, serving as a useful, low-pressure conversation starter.