Selling Pulse to LinkedIn & Scaling Notion Globally | Akshay Kothari

The Silicon Valley Influence on Career Direction

Akshay's entrepreneurial journey wasn't driven by lifelong ambition but rather by the unique environment and opportunities at Stanford:

The Quarter-by-Quarter Approach:

1. Systematic experimentation - Attempted to start a new company every quarter at Stanford
2. Clear goal orientation - Aimed to "live the American dream" rather than just get a degree
3. Multiple attempts - Five quarters of failed attempts before Pulse succeeded

Environmental Factors:

• Silicon Valley culture - The "water in the valley" created entrepreneurial aspirations
• Academic constraints - Stanford's structure provided natural experimentation cycles
• Geographic transition - Moving from Midwest (Purdue) to California opened new possibilities

Family Background Context:

• Entrepreneurial DNA - Parents and grandparents were entrepreneurs
• Marwari heritage - Cultural background with business inclinations
• Dormant influence - The entrepreneurial bug wasn't active until exposed to Silicon Valley environment

The transformation from a traditional career path to entrepreneurship happened through environmental exposure rather than inherent drive, showing how context can activate latent potential.

Timestamp: [1:46-7:57]

The Power of Academic Deadlines in Product Development

The Launchpad class at Stanford's design school created a unique pressure cooker environment that directly influenced Pulse's development:

Class Structure and Requirements:

• 11-week timeline - Extremely tight constraint for building and launching
• Public launch requirement - Students would fail if they didn't publicly launch their product
• Version 0.1 mandate - Focus on getting something out rather than perfection

Strategic Decision Making:

1. Iteration speed priority - Chose ideas that allowed multiple iteration cycles within 12 weeks
2. Travel app rejection - Abandoned travel ideas due to slow iteration potential
3. News app selection - Picked news reading because of faster development cycles

Timing and Technology Alignment:

• iPad launch coincidence - First iPad launched during the first week of class
• Market timing - Perfect alignment between new platform and class timeline
• Mid-class launch strategy - Planned to launch by middle of class for iteration opportunities

Reflection on Constraints:

Akshay believes the tight constraints prevented overthinking and may have been crucial to his eventual success. Without the forced deadline, he might have gotten stuck in analysis paralysis.

Timestamp: [2:17-5:34]

The Facebook Philosophy of Show, Don't Tell

Aditya shares a core principle from his Facebook experience that emphasizes the critical importance of tangible demonstrations over theoretical presentations:

The Mark Zuckerberg Standard:

• No slide deck reviews - Zuckerberg famously rejected presentations without working prototypes
• "Show me the prototype" - Direct demand for interactive, functional demonstrations
• Hands-on evaluation - Leaders needed to personally experience the product

SPC's Implementation:

1. Weekly demo requirement - Every member must demonstrate something each week
2. Universal application - Rule applies regardless of experience or previous success
3. Anti-intellectual salon approach - Designed to prevent endless discussion without action

Core Philosophy:

• Ideas vs. execution gap - Recognition that great ideas mean nothing without implementation
• Bytes and pixels translation - Ideas only matter when converted to actual code and design
• Prototype-driven culture - Building becomes the primary validation method

Learning Club Evolution:

SPC started as an exploration-focused learning environment but deliberately built in action requirements to ensure smart engineers would build rather than just discuss possibilities.

Timestamp: [5:40-6:57]

Essential Insights:

1. Environmental influence over innate drive - Silicon Valley's culture activated dormant entrepreneurial potential rather than fulfilling a lifelong ambition
2. Constraints as creative catalysts - Stanford's 11-week deadline and public launch requirement prevented overthinking and forced rapid execution
3. Prototype-first philosophy - Successful tech leaders prioritize working demonstrations over theoretical presentations

Actionable Insights:

• Use tight deadlines to prevent analysis paralysis and force decision-making
• Choose projects based on iteration speed potential, especially in time-constrained environments
• Implement regular demo requirements to maintain momentum and accountability
• Leverage environmental factors and peer pressure to activate latent capabilities

Timestamp: [1:02-7:57]

Early Career Transition and Silicon Valley Discovery

The Journey from India to Los Altos:

1. Family Office Experience - Packed two suitcases and moved to Los Altos to work with someone running a family office
2. Investment Learning - Spent a year working with an investor who was funding startups with his own money after his previous startup went public
3. Reality Check - Quickly realized the limitations of being a 20-21 year old trying to give advice to experienced entrepreneurs without operational experience

Key Realizations:

• Credibility Gap: Entrepreneurs weren't taking advice seriously from someone so young without proven experience
• Wrong Side of the Table: Felt uncomfortable being on the investor side without having built anything himself
• Desire to Build: Increasingly wanted to be an entrepreneur rather than an advisor

Strategic Decision:

• Stanford as a Platform: Applied to Stanford not for the degree itself, but as a structured way to meet other builders and start new ventures
• Networking Strategy: Used the academic environment as a launching pad for entrepreneurial connections

Timestamp: [8:03-9:38]

The Default Optimism and Ambition Amplification

Silicon Valley's Distinctive Mindset:

1. Curiosity Over Cynicism - Instead of calling ideas crazy, people ask "What if that were true? What if you actually pulled it off?"
2. Default Possibility - The baseline response is curiosity and openness rather than skepticism
3. Ambition Snowball Effect - Success breeds bigger ambitions: "If I can build X, why can't I build X squared?"

Contrast with Other Global Cities:

• New York/London Approach: Default cynicism with responses like "That's too hard" or "How will you get the money?"
• Silicon Valley Advantage: Never met with default skepticism, creating a beautiful environment for ambitious thinking

The Failure Embrace Culture:

• Failure as Experience: Even raising $50 million and going bankrupt can make you more attractive to investors
• Learning Premium: Going through failure is valued as educational experience
• Risk-Taking Enablement: This acceptance enables more ambitious shots and bigger swings

Present-Focused Meritocracy:

• Relevance Over History: Nobody cares if you did something good 20 years ago if you're not being ambitious today
• Youth Respect: 20-year-old founders are treated with respect based on current actions, not age
• Arena Mentality: It's about being in the arena and building, regardless of outcome

Timestamp: [10:44-13:29]

The Wrong Motivations vs. Product-First Thinking

The Problematic Startup Mentality:

• Status-Driven Motivation: Wanting to be an entrepreneur or CEO just for the title is fundamentally flawed
• Silicon Valley Pressure: The culture makes starting a company feel like the default path, with corporate jobs as "plan C"
• Getting It Out of Your System: Sometimes you need to do a startup just to satisfy the urge, even if it's for the wrong reasons

The Evolution to Product Focus:

1. Early Mistakes: First couple of ventures were driven by wanting to be an entrepreneur
2. Mindset Shift: By the time of Pulse, the focus changed completely
3. Product-Centric Approach: "I really don't care what happens to this company. What I care about is I am using this product every day to read news and other people are doing it"

Key Learning:

• User Value Over Status: Success comes from solving real problems for real users, not from achieving entrepreneurial status
• Daily Use Test: The best validation is when you and others genuinely use and need the product every day
• Authentic Motivation: Building something you personally care about and use leads to better outcomes than chasing titles

Timestamp: [9:53-10:44]

From College Project to Company Overnight

The Unexpected Moment:

• Complete Surprise: Had no idea Steve Jobs would mention Pulse at WWDC
• Still in College: This happened just three weeks before graduation while still in class
• Instant Transformation: Overnight, Pulse became a real company thanks to Jobs' blessing

The Meeting Experience:

1. Not Immediate: Didn't get to meet Jobs right after the WWDC mention
2. Later Encounter: Met him a few months later in mid-2010
3. Timing Context: This was 3-4 months after the iPad had launched
4. Personal Impact: Described Jobs as someone you "deeply respect" and "one of a kind"

The Humanizing Effect:

• Demystifying Success: Meeting successful founders and CEOs in Silicon Valley reveals they're not superhuman
• Casual Encounters: Story of walking with Mark Zuckerberg for a block while he went to get a haircut
• Accessibility: These incredible leaders are approachable and normal people
• Inspirational Realization: Understanding that "all the things you see around you are made by people no smarter than you"

Timestamp: [14:49-15:59]

Essential Insights:

1. Geographic Advantage - Silicon Valley's unique culture of default optimism and curiosity over cynicism creates an environment where ambitious ideas can flourish
2. Motivation Matters - Starting a company just to be an entrepreneur is fundamentally flawed; the best ventures come from solving problems you personally experience and care about
3. Failure as Education - Silicon Valley's embrace of failure as learning experience enables bigger risks and more ambitious pursuits

Actionable Insights:

• Focus on building products you use daily rather than chasing entrepreneurial status
• Leverage environments that default to possibility rather than skepticism for ambitious projects
• Understand that successful founders are regular people, not superhuman figures - this accessibility makes success feel achievable

Timestamp: [8:03-15:59]

Media Industry Recognition and Celebrity Encounters

The Conference Invitation:

• Jason Herson's Email: Invited Akshay to speak at Rupert Murdoch's exclusive two-day conference for editors at his ranch
• Industry Context: Peak interest in journalism's future and digital media disruption
• Pulse's Position: Two Stanford students with no backend system had created a top App Store news app

The Fireside Chat Experience:

1. Audience: 75 editors from major publications
2. Rupert's Presence: Sat in the front row center, listening intently all day
3. Personal Invitation: Murdoch personally invited them to dinner that evening

The Steve Jobs Encounter:

• Helicopter Arrival: Steve Jobs arrived by helicopter as the surprise dinner guest
• Wall Street Journal Critique: Jobs criticized the WSJ app for taking 10 seconds to launch
• Pulse Recognition: When asked about news apps he liked, Jobs specifically mentioned Pulse again
• Brief Meeting: Akshay got to spend a few minutes with the Apple CEO

This serendipitous meeting showcased how Pulse had captured attention at the highest levels of both media and technology industries.

Timestamp: [16:04-17:49]

Strategic Decision-Making and Founder Burnout

The Business Reality:

• User Base: 30 million users with strong engagement
• Publisher Network: Partnerships with 750 publishers
• Core Problem: Had millions of readers but knew nothing about them personally

The Shifting Market Need:

1. Original Problem Solved: Reading news on mobile devices was no longer a pain point after 3 years
2. New Challenge: Content overload and personalization became the primary user need
3. Failed Solutions: Collaborative filtering and recommendation attempts weren't effective
4. Missing Piece: Identity and network data to understand user preferences

The Personal Factor:

• Founder Exhaustion: Both co-founders were tired after three years of intense growth
• Role Drift: Akshay had become more of an HR person than a product builder
• Lost Joy: No longer building products, which was his primary passion

The Decision Process:

• Independent Assessment: Both founders separately wrote down acceptable acquisition prices
• Price Range: Akshay wrote ~$40M, Ankit wrote ~$50M
• Strategic Choice: Decided to explore acquisition before raising another funding round

LinkedIn's Perfect Fit:

• Complementary Assets: LinkedIn had deep identity, network, and professional data but no content
• Speed: From first phone call to signed term sheet in just four days
• Long-term Success: 12 years later, many Pulse team members still run LinkedIn's homepage relevance

Timestamp: [17:54-21:37]

Post-Acquisition Success and Long-term Impact

Team Retention and Growth:

• Exceptional Retention: Out of 25 people who joined LinkedIn through the acquisition, many stayed over 10 years
• Leadership Roles: Former Pulse team members now run LinkedIn's homepage relevance systems
• Career Success: Team members found great professional homes and advancement opportunities

Business Impact at LinkedIn:

1. Revenue Transformation: LinkedIn now makes more money from homepage content and media solutions than from recruiting
2. Product Excellence: The LinkedIn newsfeed became surprisingly effective and relevant
3. Strategic Value: Proved to be incredibly valuable for both companies long-term

Professional Network Benefits:

• Content Quality: LinkedIn feed shows relevant content about professional network contacts
• Marketing Channel: Became an excellent platform for companies to share their message
• Sustained Success: The acquisition journey had ups and downs but ultimately delivered exceptional value

Personal Reflection:

• Pride in Impact: Akshay feels extremely proud of the value created through the acquisition
• Team Success: Seeing so many team members thrive for over a decade validates the decision
• Strategic Vindication: The long-term success proved the acquisition was mutually beneficial

Timestamp: [21:17-22:36]

The Paradox of Silicon Valley Timing

The Dual Reality:

• Quick Takeoffs: Things can gain traction and scale rapidly in the tech ecosystem
• Long-term Building: True seismic change and great companies take 8-10 years to develop
• Product Development: Even within successful companies, building great products requires extended timelines

The LinkedIn News Example:

1. Immediate Integration: Pulse technology was quickly incorporated into LinkedIn
2. Long-term Evolution: It took years for the news feed to become truly excellent
3. Sustained Investment: Required patience from leadership to see the full vision realized

The Challenge for Founders:

• Necessary Impatience: Silicon Valley benefits from hunger and urgency that drives innovation
• Required Patience: Must be balanced with long-term thinking and sustained commitment
• Tricky Balance: No exact formula exists for getting this timing right

Leadership Factors in Success:

• Jeff Weiner's Vision: Previous LinkedIn CEO was deeply invested in content strategy
• Ryan Roslansky's Sponsorship: Current CEO provided long-term support and patience
• Executive Patience: Leadership's long-term commitment was crucial for the project's success

South Park Commons Philosophy:

• Ongoing Discussion: Regular conversations about balancing speed with patience
• Practical Approach: "Be impatient but take your time" - maintaining urgency while allowing for proper development
• No Perfect Answer: Acknowledging this remains a challenging balance without clear guidance

Timestamp: [22:36-23:56]

Essential Insights:

1. Celebrity Recognition - Pulse gained recognition from industry titans like Rupert Murdoch and Steve Jobs, validating its market impact
2. Strategic Acquisition Logic - LinkedIn's identity data perfectly complemented Pulse's content distribution, creating mutual value
3. Founder Decision Framework - Both co-founders independently assessed acceptable exit prices before exploring acquisition options

Actionable Insights:

• Know When to Pivot: Recognize when market needs shift and your original solution becomes commoditized
• Assess Personal Sustainability: Evaluate whether you're still doing work that brings you joy and energy
• Seek Complementary Partnerships: Look for companies with assets that perfectly complement your weaknesses
• Balance Speed with Patience: Maintain urgency while allowing time for long-term value creation
• Prioritize Team Outcomes: Consider how decisions will impact your team's long-term career success

Timestamp: [16:04-23:56]

Strategic Patience vs Tactical Urgency

The Dopamine-Serotonin Balance Framework:

1. 10-Year Vision - Maintain long-term conviction and strategic direction
2. 3-Month Dopamine Hits - Create regular progress milestones for motivation
3. Biological Balance - Avoid erratic behavior by balancing both neurotransmitters

Key Implementation Principles:

• Long-term patience with unwavering conviction in your chosen path
• Short-term impatience with sense of urgency for weekly deliverables
• Organizational Design - Teams need to feel progress toward long-term goals
• Progress Validation - Regular wins that align with ultimate vision

The Challenge:

• Easy to articulate in theory, extremely difficult to execute consistently
• Organizations rarely wait 5 years for validation of their efforts
• Requires disciplined focus on meaningful progress markers
• Balance prevents both stagnation and reactive decision-making

Timestamp: [24:01-25:01]

The Lego Philosophy of Software

The Core Problem Identified:

• Appliance Software - Every application does one specific thing (like a toaster)
• Tool Proliferation - Users surrounded by 100+ specialized applications
• Fragmented Workflow - Notes here, tasks there, project management elsewhere
• Rigid Systems - No customization for individual thinking patterns

The Building Blocks Solution:

1. Universal Primitives - Database bases, relational connections, visualization tools
2. Customizable Software - Users build tools matching their brain's workflow
3. Lego Inspiration - Same blocks, infinite creative possibilities
4. Unified Platform - All software built from identical underlying components

Technical Insight:

• Common Foundation - Jira, Greenhouse, Salesforce all use same core: databases, relations, automation
• Primitive Access - Give users direct access to these building blocks
• Personal Customization - Build software that matches individual thinking styles

The Reality Check:

• 4-Year Development - No product launch while perfecting the vision
• Team Scaling Challenge - Grew to 12 employees, then back to 2 (Ivan and Simon)
• User Behavior Learning - People don't wake up wanting to build software
• Job-Focused Reality - Users want to accomplish work, not create tools

Timestamp: [26:57-29:01]

The Strategic Wedge Approach

The Fundamental Learning:

• User Reality - People wake up to do their job, not build software
• Pre-AI Era - Only way to build software was learning to code
• Market Timing - No natural language programming available yet
• Pivot Necessity - Need entry point into users' daily workflows

The Productivity Wedge Strategy:

1. Notes and Docs - Familiar, unchanged category for years
2. Wiki Functionality - Team knowledge management needs
3. Easy Entry Point - Simple concept users immediately understand
4. Trojan Horse Approach - Start simple, expand capabilities over time

Launch Timeline and Results:

• Late 2016/Early 2017 - Productivity-focused launch
• Unexpected Demand - Latent market need for modern productivity tools
• Rapid Growth - Company "really took off" after launch
• 2018 Database Integration - Major inflection point with structured + unstructured content

Strategic Acceptance:

• Frustrating Perception - Many still see Notion as "just note-taking"
• Starting Point Philosophy - Accept initial categorization as entry strategy
• Long-term Vision Intact - Building blocks dream remains, with practical path
• User Adoption First - Get into daily workflows before revealing full potential

Timestamp: [29:13-30:40]

The Investor-to-Operator Journey

The Investment Origin Story:

• First Investment - Notion was Akshay's inaugural investment after LinkedIn acquisition
• 2013 Connection - Ivan was a designer Akshay tried to hire at Pulse
• Inkling Detour - Ivan went to Inkling instead of Pulse initially
• Seed Investment - Immediate investment after seeing Ivan's pitch deck
• Long-term Support - Close confidant through company's ups and downs

The 2018 Joining Decision:

• Serendipitous Timing - Not a calculated career move
• Mission Alignment - Always enamored by Notion's vision
• Database Integration - Joined when structured + unstructured content merged
• Rare Path - Uncommon Silicon Valley trajectory from investor to operator

The Strategic Context:

• Company Status - Well-known but not universally recognized rocket ship
• Risk Assessment - Taking bet on 5-10 year commitment
• First Principles Thinking - Decision based on mission conviction
• Personal Operating System - 7-year power user perspective informed decision

The Unique Dynamic:

• Investor Insight - Deep understanding of company's journey and challenges
• Product Conviction - Personal experience as heavy user
• Relationship Foundation - Established trust and shared vision with Ivan
• Timing Alignment - Major product inflection point coincided with availability

Timestamp: [30:49-31:55]

Essential Insights:

1. Strategic Balance - Successful companies need 10-year vision with 3-month dopamine hits to maintain organizational momentum and avoid erratic behavior
2. Building Blocks Vision - Ivan's original concept treated software like Lego blocks, recognizing that most applications (Jira, Salesforce, Greenhouse) share identical underlying primitives
3. Pivot Learning - After 4 years without launch, Notion learned people don't wake up to build software—they wake up to do their jobs, requiring a productivity wedge strategy

Actionable Insights:

• Use productivity tools as entry points while maintaining larger platform ambitions
• Accept initial market categorization as stepping stone to broader vision
• Balance long-term conviction with short-term progress validation for team motivation
• Recognize when user behavior research contradicts product assumptions and pivot accordingly

Timestamp: [24:01-31:55]

The Serendipitous Sign That Changed Everything

Akshay initially turned down Ivan's offer to join Notion as co-founder, citing his settled life in India with an 18-month-old daughter and the major life changes required.

The Unexpected Turn:

1. Initial Rejection - Despite Ivan's compelling offer to handle everything except product, Akshay said no due to family stability concerns
2. The Sign - Two days later, their nanny called from India saying she had to move back to her village due to family issues
3. The Realization - Akshay interpreted this as a clear sign from the universe that they needed to make new roots anyway

The Decision Process:

• Two-month convincing period - It took significant time to convince his wife Mana to make the move
• Major sacrifices - They were building a new home in India and had established a comfortable life
• Unknown territory - Nobody in India knew about Notion, and even people in the US questioned the decision

The Philosophy Behind It:

"This is a sign because I feel like okay, like everything is we have to make new roots or whatever, right? We have to like everything is, you know, you can't take anything for granted."

The butterfly effect demonstrates how small, seemingly unrelated events can dramatically alter life's trajectory and create opportunities for major decisions.

Timestamp: [32:02-35:55]

Building Good Stuff with Interesting People

Akshay reveals his core philosophy that transcends traditional success metrics and focuses on intrinsic motivation.

Primary Motivation Framework:

1. Mission Over Money - Being drawn to the mission and the excitement of building in a garage environment
2. People-Centric Approach - Prioritizing collaboration with interesting, talented individuals
3. Product Excellence - Focusing on creating meaningful, high-quality products

The Success Paradox:

• Controllable vs. Uncontrollable - You can do all the right things but ultimate success may still be out of your control
• Daily Focus - What you can control is coming in every day, doing great work, and pushing hard with people you care about
• Intrinsic vs. Extrinsic - Success becomes a byproduct rather than the primary driver

Key Philosophy:

"I just want to build good stuff with interesting people. And obviously, I wanted to be successful, but being successful is actually not the primary driver."

The Entrepreneurship Paradox:

• Counter-intuitive Truth - The harder you try to be a founder, the harder it becomes
• Natural Progression - Building interesting products leads to entrepreneurship, not the other way around
• Letting Go - Success requires admitting some powerlessness over immediate desires to be a founder

This approach emphasizes sustainable motivation through purpose-driven work rather than outcome-focused pressure.

Timestamp: [36:19-39:21]

Listening to Cosmic Guidance in Business

Despite being a logical, scientific person, Akshay believes in paying attention to subtle signs and synchronicities that guide major decisions.

The Universe Communication Theory:

1. Ripples Through Spacetime - The universe sends information through seemingly unrelated events
2. Active Listening - Putting your ear to what the universe is telling you
3. Confirmation Signals - When multiple signs point in the same direction

Practical Example:

• Event Planning Challenge - SPC's New York event venue fell through unexpectedly
• Previous Intuition - Akshay and Ruchi had already been discussing canceling the original venue
• Divine Confirmation - The venue falling through felt like the gods confirming their original instinct

The Balance Philosophy:

• Flow vs. Force - You have to let success flow rather than forcing it
• Lightness Approach - Being light about outcomes while maintaining focus on building
• Natural Rhythm - Finding and following the universe's rhythm instead of fighting it

Stoic Integration:

"I do feel like as I grow older, I feel like I feel more and more stoic"

Eastern Philosophy Parallels:

• Buddhist Mindfulness - Similar principles to stoic philosophy
• Control Focus - Controlling only what you can control
• Universal Rhythm - Not trying to fight the natural flow of events

This approach combines rational business thinking with intuitive awareness of environmental signals and synchronicities.

Timestamp: [37:28-40:26]

The Gratitude of Rejected Paths

Akshay reflects on how career disappointments often become blessings in disguise, particularly his failed attempt to enter investment banking.

The Investment Banking Story:

1. 2007 Graduation Goal - Really wanted to get into investment banking when graduating
2. The Rejection - Didn't get the position he desperately wanted
3. The Blessing - Now grateful he didn't get it because it would have led to a completely different career path

The Retrospective Wisdom:

• Pattern Recognition - Looking back reveals how many "failures" were actually better outcomes
• Attachment Issues - Often we hold onto things that aren't actually best for us
• Alternative Paths - The things that happened instead were probably better choices

The Stoic Growth:

"I do feel like as I grow older, I feel like I feel more and more stoic"

Key Insight:

"There's so many of the things I can look back and be like, 'Oh my god, I that had happened and I was holding on to it but the thing that alternative thing that happened actually was probably the better thing and so is a better one.'"

Life Philosophy Integration:

• Eastern Mindfulness - Similar to Buddhist principles about attachment
• Stoic Acceptance - Embracing what happens rather than fighting it
• Universal Trust - Believing that alternative outcomes often serve us better

This perspective encourages viewing career setbacks as potential redirections toward better opportunities.

Timestamp: [39:28-40:01]

Essential Insights:

1. The Butterfly Effect - Small, seemingly unrelated events (like a nanny's family emergency) can create pivotal moments that redirect entire life trajectories
2. Mission-Driven Success - Building good products with interesting people should be the primary driver, with financial success as a natural byproduct rather than the main goal
3. Universe Signals - Paying attention to synchronicities and environmental signs can guide major business and life decisions, even for logical, scientific minds

Actionable Insights:

• Embrace Uncertainty - When multiple life changes happen simultaneously, consider it might be time for a major pivot rather than fighting to maintain the status quo
• Focus on Controllables - Channel energy into daily great work and meaningful relationships rather than obsessing over ultimate outcomes
• Practice Retrospective Gratitude - Regularly reflect on how past disappointments and rejections led to better opportunities than originally planned

Timestamp: [32:02-41:35]