Anyone join a startup that actually paid a fat check at exit?

Based on the most helpful WSO content, the reality of joining a startup and walking away with a "fat check" at exit is far from guaranteed. Here are some key insights:

1. Equity Payouts Are Rarely as Lucrative as Expected:

   • Many startups fail to reach a meaningful exit. Even if they do, the equity stake for non-founders is often small, especially in VC-backed startups where investors have liquidation preferences. This means investors get paid first, and common stockholders (employees) may receive little to nothing.
   • Even at the top of the organization, equity stakes are often less than 10%, and startups are notoriously stingy about increasing equity stakes over time.

2. Risk vs. Reward:

   • The probability of a startup achieving a multibillion-dollar exit is extremely low. For example, one thread mentions that even if a startup exits at $5 billion, the expected value of equity might only slightly exceed a base salary in finance, given the low probability of such an outcome.
   • Joining a startup at an early stage (Preseed or Series A/B) does offer the potential for a higher equity stake, but the risk profile is significant. Most startups either fail or plateau, leaving employees with little financial upside.

3. Examples of Success Are Rare:

   • While there are anecdotes of individuals joining a 10-person startup, getting a meaningful equity stake, and cashing out big, these are exceptions rather than the rule. For every success story, there are countless startups that fail to deliver meaningful returns to employees.

4. Alternative Perspectives:

   • Some WSO threads suggest that if you're considering the startup route, it might be better to start your own company or join as one of the first employees. This way, you can secure a larger equity stake for a similar risk profile.
   • Others argue that the experience and exposure gained at a startup can be valuable, but the financial upside is often overstated compared to staying in IB/PE.

In summary, while the dream of a "fat check" from a startup exit is enticing, the reality is that it's a high-risk, low-probability outcome. If financial security and consistent compensation are priorities, staying in IB/PE might be a safer bet. However, if you're passionate about a startup's mission or see a genuine 100x potential, it could be worth the gamble—but go in with eyes wide open.

Sources: Why You Should Reject that Start-Up Job, Banking -> Startup PM on who SHOULD join IB, Why You Should Reject that Start-Up Job, Want to build a startup & raise some money? Part I