money money money 817 investing in the company you work for, CHESS vs non-CHESS brokers & money on first dates
Apr 28, 2025
Jess Brady, a savvy financial adviser and host of Financially Fierce, dives into the complexities of investing in your employer's company. She shares valuable tips on navigating employee share schemes, emphasizing the importance of alignment with personal goals. The conversation shifts to the pros and cons of CHESS versus non-CHESS brokers and the implications for tax reporting. Lastly, Jess tackles the quirky topic of discussing finances on first dates, suggesting light-hearted ways to approach money conversations without awkwardness. A must-listen for finance enthusiasts!
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When To Invest In Your Employer
- Do only invest in your employer if you have conviction and it aligns with your financial goals.
- Check structure, tax rules, valuation, liquidity and diversification before committing any money.
Beware Golden Handcuffs
- Employee equity can create 'golden handcuffs' and overweight personal portfolios in one company.
- Heavy ownership becomes risky if income or share value falls at the same time you lose your job.
Read The Share Scheme Fine Print
- Read the fine print: know whether you get shares, options, RSUs, discounts, vesting schedules and tax timing.
- Ask about strike price, tax triggers and how vesting or option taxation works before you accept anything.
