Should You Start a Startup? with Harj Taggar | Startup School

Introduction & Target Audience

YC Group Partner Harj Taggar addresses a fundamental question that many aspiring entrepreneurs grapple with - whether they're cut out for startup life.

Target Audience for This Talk:

1. People not ready today - Those who don't feel prepared to start a startup right now
2. Future-oriented thinkers - Individuals who think they may want to start a company someday
3. Decision seekers - Anyone uncertain about their entrepreneurial potential

Two-Part Framework:

Part 1: Founder Personality Assessment

• Identifying which types of people are best suited to being startup founders
• Self-assessment tools and insights
• Understanding your natural strengths and weaknesses

Part 2: Preparation Strategy

• How to best prepare yourself for becoming a startup founder
• Skills development and experience building
• Timeline and milestone planning

"I'm going to break down the topic of whether you should start a startup into two parts: first we'll talk about which types of people seem best suited to being startup Founders and help you figure out if you might be one of them, second we'll talk about how you might best prepare yourself for becoming a startup founder in the future." - Harj Taggar

Timestamp: [0:01-0:50]

Debunking Common Stereotypes

After working with nearly 1,000 startup founders, YC's experience reveals surprising truths about who actually succeeds in startup life.

The Stereotype Problem:

• Media portrayals create narrow definitions of successful founders
• Mark Zuckerberg archetype: Ruthless, brilliant programmer
• Steve Jobs model: Charismatic product genius
• These stereotypes exclude many potentially successful founder types

Reality Check from YC Experience:

Surprising Founder Diversity:

1. Many different types succeed - Far beyond the Hollywood stereotypes
2. Unexpected strengths matter - Different skill sets can lead to success
3. Prediction is difficult - Even experienced investors get surprised

The Prediction Challenge:

• 15 years of experience and Harj still gets surprised by who succeeds
• Traditional metrics don't predict startup success as well as expected
• School and work performance are less predictive than initially thought

"I can say that after working with many successful Founders there are many more different types of people who succeed as startups with different strengths than just those stereotypes." - Harj Taggar

Key Insight:

If experienced investors struggle to predict founder success, self-assessment becomes even more challenging - but not impossible with the right framework.

Timestamp: [0:50-2:20]

Why Traditional Success Metrics Fall Short

The startup journey involves a level of personal rejection and struggle that traditional career paths don't prepare you for.

The Unique Challenge of Startups:

Personal Investment Reality:

1. Blood, sweat, and tears required to convince even a single user
2. Massive rejection in getting your first 10-100 users
3. Personal nature of rejection - it's YOUR startup, YOUR idea being rejected
4. Different from corporate work - building someone else's product feels less personal

Why Resilience Trumps Everything:

The Core Requirement:

• Resilience is the most important quality for startup founders
• Ability to push through rejection and keep going
• Mental toughness to handle the emotional ups and downs
• Long-term persistence when progress seems impossible

Common Misconception About Confidence:

• Confidence ≠ Resilience: Initially seemed like a good proxy
• High energy and conviction don't guarantee resilience
• Quiet founders often turn out to be most resilient
• Appearances can be deceiving in startup interviews

"When you're working on a startup you have to put in Blood Sweat and Tears to convince even a single user to care about trying your product... all of that rejection feels very personal in a way it doesn't when you're working at a Fan Company building a product for someone else." - Harj Taggar

The Confidence Trap:

Many confident-seeming founders struggle when hitting real roadblocks, while quiet, less confident founders often demonstrate incredible resilience over time.

Timestamp: [2:20-3:18]

A $6 Billion Lesson in Misjudging Founders

Sajith Wickramasekara's journey from soft-spoken engineer to successful CEO demonstrates how resilience matters more than initial confidence.

Initial Concerns and Doubts:

The 2012 Interview:

• Sajith and co-founder Corey were both softly spoken engineers
• YC's concern: Wouldn't be suited for enterprise sales to biotech/pharma companies
• Investor skepticism: Demo day investors worried about their sales ability
• Funding struggle: Benchling struggled to raise much seed funding

The Long, Difficult Journey:

Timeline of Struggle:

1. Year 1 post-YC: Still making zero revenue
2. Some traction: Enthusiastic grad students using product for free
3. Product development: Software continued improving despite no sales
4. Year 2 milestone: Finally started doing sales and generating revenue
5. Total timeline: Nearly 2 years from YC to first revenue

The Remarkable Transformation:

Current Success Metrics:

• Valuation: Now worth over $6 billion
• Customer base: Many of the world's top biotech and pharmaceutical companies
• Leadership growth: Sajith transformed into a formidable founder and CEO
• Future outlook: On track to become a public company

The Resilience Lesson:

"Looking back I always had confidence that Sagi was a good engineer but I could not have predicted back when we funded him in 2012 that he would have the resilience to overcome that amount of rejection and transform himself into the leader of a company that took many years to become great at Enterprise sales." - Harj Taggar

Key Takeaway:

Even experienced investors couldn't predict Sajith's resilience. His quiet demeanor masked an extraordinary ability to persist through years of rejection and slowly build the skills needed for enterprise sales success.

Timestamp: [3:33-5:10]

Essential Insights:

1. Resilience over confidence - The ability to persist through rejection matters more than initial confidence or charisma
2. Founder diversity succeeds - Many different personality types can build successful startups beyond media stereotypes
3. Prediction is nearly impossible - Even experienced investors struggle to identify who will succeed as founders

Actionable Insights:

• Don't disqualify yourself based on not fitting the "typical founder" stereotype
• Focus on building resilience rather than just projecting confidence
• Understand that startup success often takes much longer than expected (2+ years to revenue is common)

Timestamp: [0:01-5:10]

People Mentioned:

• Harj Taggar - YC Group Partner presenting this talk on startup founder assessment
• Mark Zuckerberg - Referenced as the stereotypical "ruthless brilliant programmer" founder archetype
• Steve Jobs - Cited as the "charismatic product genius" stereotype often depicted in media
• Sajith Wickramasekara - Founder and CEO of Benchling, example of quiet resilience leading to massive success
• Corey - Co-founder of Benchling alongside Sajith

Companies & Products:

• Y Combinator - Startup accelerator that invests in early-stage companies
• Benchling - Biotech software company now worth over $6 billion, serving pharmaceutical companies
• Facebook - Referenced in context of Mark Zuckerberg's founder archetype

Books & Publications:

• The Social Network - Movie depicting Mark Zuckerberg that creates narrow founder stereotypes
• Steve Jobs biographies/movies - Various books and films about Apple's co-founder

Concepts & Frameworks:

• Resilience vs Confidence - The key distinction in founder assessment and startup success prediction
• Enterprise Sales - The challenging process of selling software to large biotech and pharmaceutical companies
• Founder Stereotypes - Media-created narrow definitions of what successful entrepreneurs should look like

Timestamp: [0:01-5:10]

Debunking the "Right Reasons" Myth

Popular startup advice suggests you need noble motivations to succeed, but YC's experience shows initial reasons matter less than you think.

Common Motivation Myths:

The "Don't Do It for Money" Fallacy:

• Popular advice: Starting a company just for money is considered flimsy
• YC's reality: It's perfectly fine to start a startup to become rich
• Economic truth: Startups are one of the few ways to make life-changing money in a short time
• Practical approach: If desire for money gets you started, that's great

Curiosity as Valid Motivation:

• Simple curiosity about founding a startup is a fine initial motivation
• Only way to know: Actually doing a startup is the only way to know if you'll enjoy it
• Experience-based learning: You can't fully understand startup life from the outside

Why Initial Motivations Don't Predict Success:

Motivation Evolution Over Time:

1. Founders change their minds - Plans to sell within a year often extend to decades
2. Companies evolve - Same startup, different vision after years of work
3. Long-term commitment - Some YC companies started with short-term goals are now public
4. Enduring motivations develop - What sustains you matters more than what starts you

"I've seen Founders who started out a company with a plan to sell it within a year change their mind as they kept working the company and they're still working on that same startup a decade later and it's now a public company." - Harj Taggar

What Actually Sustains Founders:

• Genuine interest in the problem you're working on
• Love for the people you're working with
• Deep engagement with the work itself

Timestamp: [5:15-7:05]

Practical Framework for Startup Decision-Making

Instead of endless introspection about founder suitability, focus on concrete risk assessment and worst-case scenario planning.

The Practical Approach:

Stop Over-Analyzing, Start Risk Assessment:

• Skip the introspection about whether you'll make a good founder
• Focus on practical realities of what failure looks like
• Honest evaluation of your personal situation and constraints

The "What Do I Have to Lose?" Framework:

1. Timeline reality: At least one year needed to gather meaningful data
2. Worst-case scenario: Shutting down without earning salary for that year
3. Personal assessment: Can you actually live with that outcome?
4. Honest self-evaluation: If you can't handle worst-case, anxiety will sabotage efforts

Context-Dependent Risk Calculation:

Low-Risk Scenarios:

• Recent college graduate: Job offers will still be available in a year
• Early career professionals: Limited opportunity cost
• Between jobs: Natural transition point

High-Risk Scenarios:

• FAANG employee for 9 years: Potentially missing big promotion opportunity
• Established career trajectory: Significant opportunity cost to consider
• Financial obligations: Family, mortgage, or other commitments

"If you're about to graduate college taking a year after graduating to work on a startup is not a big deal those job offers will still be waiting for you in a year but if you've been a Fang employee for the past nine years and you're in line for a big promotion this year then maybe you stand to lose a lot." - Harj Taggar

The Self-Sabotage Warning:

If you can't actually handle the worst-case scenario, your constant anxiety will likely undermine your startup efforts before external factors do.

Timestamp: [7:05-8:25]

Why Startup Experience Is Undervalued in Risk Calculations

Most people don't factor in the immense learning value when calculating startup risk, but this education can be career-transforming regardless of startup success.

The Comprehensive Learning Experience:

Multi-Functional Skill Development:

• Everything is your responsibility as a startup founder
• Diverse work exposure: Sales, product development, customer support simultaneously
• Career clarity: Helps identify what type of work you truly enjoy
• Specialization insights: Discover where you want to focus your career

Two Common Post-Startup Paths:

1. Serial entrepreneurs: Learn from mistakes and start another company immediately
2. Specialized professionals: Join companies to focus on one area they discovered they love

Market Value of Startup Experience:

Employer Perspective Benefits:

• Self-starter evidence: Demonstrates initiative and leadership capability
• Project leadership: Shows ability to take charge and drive results
• Risk tolerance: Indicates comfort with uncertainty and challenge

Real-World Hiring Advantages:

From Harj's experience with TripleByte (his second startup):

• Hundreds of employers explicitly sought people with startup experience
• Premium placement: Former founders often hired for leadership roles
• Career acceleration: Startup experience opens doors that traditional paths don't

"The startup experience can really improve your career opportunities even if the startup doesn't succeed... many of them were explicitly looking to hire people who had previous startup experience they believe they showed evidence of being a self-starter and being able to take initiative and Lead projects." - Harj Taggar

Timestamp: [8:25-9:35]

Real Examples of Startup Experience Creating Career Gold

Two powerful examples show how startup experience, even from "failed" companies, can lead to extraordinary career outcomes.

Rippling's Founder-Focused Hiring Strategy:

The $10 Billion Company Approach:

• Company: Rippling, valued at $10 billion
• Founder: Parker Conrad (also YC alum)
• Hiring philosophy: Actively recruits former founders
• Organizational structure: Former founders run entire product divisions
• Scale: Approximately 50 former founders now work at Rippling

Strategic Reasoning:

"Usually we love hiring former Founders to run specific product lines and and build them and and really run them as general managers we've been you know really successful at recruiting." - Parker Conrad

This demonstrates how startup experience translates directly into general management and product leadership roles at scale.

Nick Grandy's Non-Linear Career Journey:

The Serendipitous Path:

1. 2008: YC funded his first startup, Wanderfly
2. Startup outcome: Company shut down (apparent "failure")
3. Career pivot: Joined another YC company as first employee
4. The company: Airbnb (you may have heard of it)
5. Long-term success: Spent many years helping build Airbnb
6. Second act: Left to start Outschool, now valued at over $3 billion

Key Insight on Career Progression:

"I share these stories to show how career progressions are not always perfectly linear introducing some Serendipity and meeting smart ambitious people can completely transform your career and being a startup founder is a great way to do exactly that." - Harj Taggar

The Network Effect:

• Smart, ambitious people: Startup ecosystem connects you with high-caliber individuals
• Serendipitous opportunities: Non-linear career paths often lead to bigger outcomes
• Ecosystem benefits: YC companies regularly hire talent from other YC companies
• Compound growth: One startup experience opens doors to multiple future opportunities

Timestamp: [9:35-10:49]

Essential Insights:

1. Initial motivations are overrated - What sustains you long-term matters more than what gets you started, and motivations naturally evolve over time
2. Risk assessment beats introspection - Focus on practical worst-case scenarios rather than endless self-analysis about founder suitability
3. Startup experience has hidden value - The learning and career opportunities from startup experience are often undervalued in risk calculations

Actionable Insights:

• Calculate your personal worst-case scenario honestly and decide if you can live with it
• Factor in the learning value and career boost from startup experience when assessing risk
• Consider that "failed" startups often lead to extraordinary career opportunities through networks and experience
• Don't worry about having the "right" initial motivations - curiosity and financial goals are perfectly valid starting points

Timestamp: [5:15-10:49]

People Mentioned:

• Harj Taggar - YC Group Partner sharing insights on startup motivations and risk assessment
• Parker Conrad - Founder of Rippling, discussing their strategy of hiring former founders
• Nick Grandy - Former founder of Wanderfly, first employee at Airbnb, founder of Outschool

Companies & Products:

• TripleByte - Harj's second startup that helped companies identify and hire talent
• Rippling - $10 billion company that actively hires former founders for leadership roles
• Wanderfly - Nick Grandy's first startup that shut down but led to career opportunities
• Airbnb - Company where Nick became first employee after his startup failed
• Outschool - Nick's second startup, now valued at over $3 billion
• Y Combinator - Startup accelerator connecting founders and creating career opportunities

Concepts & Frameworks:

• "What Do I Have to Lose?" Framework - Practical risk assessment method for startup decision-making
• Motivation Evolution - How founder motivations naturally change and develop over time
• Network Effects in Careers - How startup ecosystems create serendipitous career opportunities
• Worst-Case Scenario Analysis - Method for honest evaluation of startup risks and personal readiness

Timestamp: [5:15-10:49]

Strategic Preparation When You're Not Ready Today

If you've decided you can handle the worst-case scenario but aren't ready to start immediately, here's how to strategically prepare for your entrepreneurial future.

The Two Essential Components:

What You Need to Start:

1. An idea - Something worth building and solving
2. A co-founder - Someone to build it with

The Reality of Timing:

• Sometimes both come quickly - Idea and co-founder appear simultaneously
• Usually takes time - Most people need preparation period
• Lots of great content exists - For when you're ready to start
• Gap in guidance - Less advice for the preparation phase

The Integrated Approach:

Why Not to Separate Ideas and Co-founders:

• Ideas are hard to generate alone - Brainstorming in isolation is difficult
• Ideas start vague and fuzzy - More like hunches or impulses initially
• Iteration is essential - Takes several rounds to make ideas concrete
• Discussion improves ideas - Talking through concepts with others is crucial
• Best person to discuss with - Your future co-founder

"I'd start by encouraging you to not think of finding ideas and co-founders as two separate tasks. It's hard to think up good ideas yourself also your ideas will start out being vague and fuzzy more like a hunch or an Impulse than a clearly formed idea." - Harj Taggar

The Conversation-Driven Method:

Best ideas emerge during conversations with smart people, making relationship-building and idea generation naturally interconnected processes.

Timestamp: [10:55-11:51]

Identifying and Cultivating Relationships with Potential Collaborators

The key to finding both great ideas and co-founders lies in identifying people you naturally collaborate well with and enjoy intellectual discussions.

Identifying Potential Co-founders:

In College Environment:

• Problem-solving partners - People you turn to when stuck on hard problems
• Group project favorites - Colleagues you most enjoy working with on assignments
• Natural collaborators - Those who make group work actually enjoyable

In Work Environment:

• Productivity multipliers - Colleagues who make you more productive
• Performance enhancers - People who help you do your best work
• Intellectual stimulators - Those who challenge and inspire your thinking

The Conversation Strategy:

Topics to Explore Together:

1. Interesting technologies - Discuss emerging tech and its potential
2. Daily product experiences - Talk about products you admire or find frustrating
3. Underrated technologies - Debate why certain tech is undervalued today
4. Industry observations - Share insights about market gaps and opportunities

The Research Component:

• Between conversations - Do your own reading and research
• Deepen knowledge - Learn more about topics that interest you
• Prepare for discussions - Come with informed perspectives
• Natural curiosity - This should feel engaging, not forced

"I'd see these people out and start having conversations with them about ideas or technologies that you find interesting. Talk about products you use every day that you admire or are frustrated by." - Harj Taggar

Dual Benefits of This Approach:

1. Primes your mind - Makes you more likely to notice potential startup ideas
2. Evaluates relationships - Helps assess friends/colleagues as potential co-founders

Environment Change Warning:

If you're struggling to find people you enjoy discussing ideas with, you probably need to change your environment and meet new people.

Timestamp: [11:51-12:48]

Strategic Career Moves for Future Founders

To maximize your chances of finding great co-founders and understanding startup dynamics, choose environments where you'll be surrounded by entrepreneurial-minded people.

Why Startups Are the Ideal Environment:

Insider Knowledge Benefits:

1. See how startups work - Get firsthand experience of startup operations
2. Understand the mechanics - Learn the real challenges and processes
3. Witness decision-making - Observe how startup leaders think and act
4. Experience the culture - Understand startup pace and priorities

Co-founder Discovery Advantages:

• Less risk-averse colleagues - Startup employees are naturally more entrepreneurial
• Shared mindset - Surrounded by people interested in building companies
• Natural selection - People who choose startups often have founder potential
• Common goals - Colleagues who might someday want to start their own companies

Strategic Career Path Recommendations:

For College Students:

• Find a startup to work at after graduation
• Skip traditional corporate roles initially
• Gain startup experience early in your career

For Current FAANG Employees:

• Consider leaving to join a startup as an intermediate step
• View it as preparation for starting your own company someday
• Strategic career move rather than permanent departure from big tech

"If you really want to start a company one day it's best to choose an environment where you will be around many people who might someday be your co-founder. I think the best environment for this is working at a startup." - Harj Taggar

The Network Effect:

Working at startups naturally connects you with people who have both the skills and mindset needed for entrepreneurship.

Timestamp: [12:48-13:23]

Building Your Entrepreneurial Muscles Through Small Experiments

Once you're having great conversations with potential co-founders, the next step is learning to turn ideas into reality through side projects.

The Side Project Progression:

From Conversation to Action:

1. The magic moment - When someone says "It'd be cool if someone built X"
2. Stop and think - How could YOU be the one to build X?
3. Simplify the concept - What's a simple first version you could build over a weekend?
4. Find potential users - Who might use this and how do they react to the idea?
5. Create a plan - Turn the concept into something real, however small

Managing Expectations:

• Not launching a unicorn - You're not trying to build the next billion-dollar company
• Building experience - Getting used to turning ideas into reality
• Experiencing the thrill - Learning what it feels like to launch something
• Skill development - Practicing the entrepreneurial process

Essential Technical Skills:

The Programming Requirement:

• Two paths available: Learn to program yourself OR find a technical co-founder
• Recommended approach: Learn to code yourself
• Skill level needed: Only enough to build version one of your ideas
• Experience matters: Speaking from someone who started without coding ability

"If you're not a programmer then either you need to learn how to program or find a co-founder who is a programmer. My advice speaking from experience as someone who started his first startup without being able to code: you start learning to code." - Harj Taggar

Why Learning to Code is Recommended:

• Independence - Don't depend on finding technical co-founder immediately
• Better communication - Understand what's technically feasible
• Credibility - Technical co-founders respect founders who can code
• Speed - Build and iterate faster in early stages

Timestamp: [13:23-14:27]

Knowing When Your Side Projects Are Ready to Become Your Main Focus

The transition from side projects to full-time startup isn't always obvious. Here's how to read the signals and make the decision.

The Traction Reality Check:

Don't Wait for Explosive Growth:

• Ideal scenario: Side project gets explosive traction and makes decision easy
• Reality: You can't rely on that happening
• Mixed feedback is normal - Early users will have varied reactions
• Spectrum of responses - Users will be delighted, appalled, or indifferent

Paul Buchheit's Quality Over Quantity Principle:

The Love vs. Indifference Test:

"It is better to make a product that a few people really love than one a lot of people are indifferent towards." - Paul Buchheit

Signs You're Onto Something:

• Deep reaction from users - Someone has a strong emotional response
• Behavioral change - Users do something very differently because your product exists
• Legitimate transformation - Real impact on how people work or live
• Passionate users matter more than large numbers

Value Hierarchy:

• One passionate user of a crude weekend prototype
• Beats a million signups on a waitlist for something that doesn't exist yet
• Quality of engagement over quantity of interest

Focus on Process, Not Just Results:

Internal Assessment Questions:

1. Enjoyment factor - How much are you enjoying the process of thinking up ideas and building them?
2. Learning curve - Are you learning new things and feeling energized?
3. Energy comparison - How does this feel compared to your day job?
4. Work-life energy - If your job drains you but side projects energize you, that's a signal

The Co-founder Chemistry Test:

• Collaboration enjoyment - Do you genuinely enjoy working with your side project collaborators?
• Shared ambition - Do you both want to be startup founders?
• Recognize rarity - Having a great potential co-founder is rare and valuable
• Sufficient reason - This alone can be a fantastic reason to quit and start a company

"Pay particular attention to how much you enjoy working with your side project collaborators. If you enjoy working with them and you both want to be startup Founders recognize how rare that is." - Harj Taggar

Timestamp: [14:27-16:17]

Complete Summary of Actionable Steps for Future Founders

Harj wraps up with a comprehensive action plan for anyone serious about starting a company in the future.

Core Mindset Principles:

1. Don't Overthink Initial Motivations:

• Motivations can change over time as you grow and learn
• Curiosity is sufficient - Simply being curious about the startup experience is enough to get started
• Perfect reasons aren't required - You don't need noble or profound motivations

2. Practical Risk Assessment:

• Think worst-case scenario - What happens if you start a company and it fails?
• Honest evaluation - Be sure you can actually live with that outcome
• No self-deception - If you can't handle the worst case, wait until you can

Actionable Preparation Steps:

3. Build Your Network and Skills:

• Find smart people to talk about ideas with regularly
• Launch side projects - However small, get experience turning ideas into reality
• Actually launch - Don't just plan or discuss, ship real products
• Gain practical experience - Learn what it feels like to build and release something

4. Recognize the Right Partnership:

• Find someone you enjoy working with on side projects
• Shared entrepreneurial ambition - Both of you want to start a company
• Make the jump together - Don't wait for perfect timing when you have great partnership

The Invitation:

"I really hope you do and I hope we get to work together at YC Community someday." - Harj Taggar

YC's Open Door:

The talk concludes with an invitation to join the Y Combinator community, emphasizing that YC wants to work with people who take this preparation process seriously.

Final Encouragement:

Starting a company is one of the most rewarding and challenging things you can do. With proper preparation, risk assessment, and the right partnership, you can increase your odds of success significantly.

Timestamp: [16:17-17:03]

Essential Insights:

1. Integration beats separation - Don't treat finding ideas and co-founders as separate tasks; the best approach combines both through collaborative conversations and side projects
2. Environment shapes opportunities - Working at a startup puts you around entrepreneurial people and gives you insider knowledge of how startups actually operate
3. Process matters more than results - Focus on whether you enjoy building things and working with collaborators rather than waiting for explosive traction

Actionable Insights:

• Start having regular conversations about interesting technologies and product ideas with smart people you enjoy working with
• Consider joining a startup as a strategic career move to surround yourself with potential co-founders
• Launch small side projects to practice turning ideas into reality, focusing on finding users who love your product rather than large numbers
• Learn basic programming skills to build version one of your ideas independently

Timestamp: [10:55-17:03]

People Mentioned:

• Harj Taggar - YC Group Partner providing comprehensive advice on startup preparation and timing
• Paul Buchheit - YC Partner whose principle "better to make a product a few people love than many people are indifferent towards" guides startup validation

Companies & Products:

• Y Combinator - Startup accelerator mentioned as destination for future founders

Concepts & Frameworks:

• Love vs. Indifference Principle - Paul Buchheit's framework for evaluating startup idea validation
• Side Project Strategy - Method for building entrepreneurial skills through small experiments
• Worst-Case Scenario Analysis - Risk assessment framework for startup decision-making
• Co-founder Discovery Process - Integrated approach to finding ideas and partners simultaneously
• Startup Environment Strategy - Career positioning approach for future founders

Timestamp: [10:55-17:03]