Don't wait for an external sign to ask for a raise or equity. The internal feeling that you are undervalued is the sign itself. The act of formulating the question "When should I ask?" indicates that the time to have that difficult conversation is now.

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You cannot consistently achieve an income level that you don't subconsciously believe you deserve. Your internal self-worth dictates your confidence and ability to make the necessary asks to reach higher earnings.

To maintain an owner's mindset, the speaker asked his new employer not to tell him the total number of company shares. This counterintuitive move prevented him from being demotivated by a small percentage and signaled extreme commitment, which ultimately led to his stake increasing from 0.4% to 20%.

Granting stock options is only half the battle. To make equity a powerful motivator, leaders must constantly communicate a clear and believable narrative for a future liquidity event, such as an acquisition. This vision is what transforms paper ownership into a tangible and valuable incentive in the minds of employees.

When you have a better offer, present it to your manager as a difficult decision. Emphasize your loyalty and desire to stay, but explain the other offer is compelling. This approach opens a collaborative dialogue about your value and compensation rather than creating a confrontational standoff.

Passion has a dark side in the workplace. Highly passionate individuals are often less likely to negotiate their salary because they worry that bringing up money will make others doubt the authenticity of their commitment. This can lead to them being underpaid and exploited.

To keep high-performers, beyond giving them equity, you must explicitly map out their trajectory. Galloway advises sitting down with employees to define their position, responsibilities, and financial standing three years into the future. This clarity on growth and demonstrated investment in their success is highly "intoxicating" for ambitious individuals.

When management denies your request for a new opportunity, resist the urge to immediately see it as a red flag. First, critically assess your own strategy. Are you communicating in a way your audience understands? Are you trying to skip essential learning steps? Self-correction is often more valuable than immediately leaving.

When negotiating a job offer, ask for more stock options instead of a higher salary. This is often better received by employers as it signals you are a long-term believer in the company's success and want to be an "owner," not just an employee.

Founders often assume employees share their risk appetite for equity, but this is a mistake. When offered a choice between a higher cash salary and a mix of cash and equity, the vast majority of employees will choose the guaranteed cash, revealing a fundamental aversion to risk.

Instead of directly asking for a raise, top salespeople should request better opportunities like bigger accounts or higher-quality leads. This frames the conversation around driving more revenue, which speaks a sales manager's language and demonstrates a focus on performance over entitlement, making it a more effective negotiation tactic.