Should You Start A Startup?

Executive Summary:

  • Key qualities for successful startup founders include resilience, not just confidence. Motivations can evolve, and startup experience is valuable even in failure.

  • Finding a co-founder and an idea go hand-in-hand. Developing necessary skills, recognizing the right time to take the leap, and embracing the startup experience are crucial preparation steps.

Meeting Notes:

Whether you should start a startup

  • Characteristics of successful startup founders

    • Not just brilliant programmers or charismatic product geniuses

    • Resilience is a crucial quality

    • Some seemingly quiet and unconfident founders initially (like Harj Taggar's example of Sagi, founder of BenchLink) turned out to be highly resilient

    • Confident founders sometimes struggled when facing roadblocks

    • Harj Taggar cautions against using confidence alone as a proxy for resilience

  • Motivations for starting a startup

    • Desire to make money is a legitimate motivation

    • Curiosity about the startup experience is also fine as an initial motivation

    • Harj Taggar has seen founders whose motivations changed over time, sticking with their startup for over a decade despite initially planning a quick exit

  • Assessing if you can handle the worst-case scenario

    • Understand the downside risk (e.g. going a year without much/any salary)

    • Factor in the valuable learning experience of starting a company

    • Can help figure out types of work you enjoy

    • Harj Taggar notes many employers value startup experience as showing initiative and ability to lead projects

    • Some successful companies like Rippling explicitly hire and empower former founders

Preparing to become a startup founder

  • Finding a co-founder and an idea

    • The two go hand-in-hand, difficult to pursue separately

    • Seek out people you enjoy discussing ideas with (friends, colleagues)

    • Start experimenting with side projects to turn ideas into reality

  • Developing the necessary skills

    • Learn to code if you're not a programmer already
  • Recognizing when to take the leap

    • Look for: A few deeply passionate users of your crude prototype (more valuable than many indifferent signups)

    • Energizing feeling from the idea/project process vs draining day job

    • Enjoyable collaboration with potential co-founder

  • Advice for taking the next steps

    • Don't overthink your initial motivations

    • Embrace the startup experience by:

    • Surrounding yourself with potential co-founders (e.g. working at a startup)

    • Launching basic versions of ideas as side projects

    • Quitting job to co-found with someone you truly enjoy working with on those projects