In my 15-year journey across tech, I’ve learned that deciding which new venture to join, especially as a founding engineer, is an art in itself. Through my experiences, I’ve distilled essential criteria that I always use to evaluate a startup’s health and its impact on the quality of work life.

Technical Co-founder Presence: Assess if the founder has a technical co-founder. Without one, you may end up performing their duties without appropriate compensation.

Founder’s Venture Experience: Consider whether the startup is the founder’s first venture. Previous successes or failures can impart valuable experience, whereas a first-time founder may face significant learning curves and failures.

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Financial Runway: Evaluate the startup’s financial runway, i.e., how many months it can operate before running out of funds. A good startup should have a sufficient runway, ideally up to two years, to reach product-market fit.

Founder-Investor Relationship: Investigate the relationship between the founders and their investors. A bad relationship can create internal friction and distract from achieving product-market fit.

Startup’s Funding Source: Understand how the startup is financing its operations. Founders using personal savings may be more risk-averse and controlling, whereas external funding might lessen the pressure.

Founder’s Industry Relevance: Check if the founders have experience in the industry of their startup. Lack of industry knowledge can lead to misjudging the market and the viability of the solution.

Perception of Engineering: Gauge how the founder perceives engineering work. Some may undervalue it or consider outsourcing it, while others might overemphasize it at the expense of business outcomes.

Shadow Stakeholders: Look out for hidden stakeholders who may influence decision-making, limiting the founder’s ability to effect positive changes quickly.

Presence of Advisors: Be wary of founders surrounded by numerous advisors, as their advice may be generic and not actionable, showing a lack of commitment to the startup’s specific challenges.

Founder’s Management Style: Consider if the founder is a micromanager, which can lead to focusing on trivial details over more critical aspects like product development and market fit.