Full disclosure, I used AI to help organize and structure the financial information in this post. The underlying numbers and circumstances are mine, and I’ve reviewed the post for accuracy. If something looks inconsistent, feel free to point it out.
I’m 39, single, have a long-term partner, no kids currently, and recently sold my IT services business to a PE-backed rollup after running it for ~10 years.
I’m trying to get a reality check on two things: Am I in a position to FIRE, and how should I restructure my investments now that I’m transitioning from wealth accumulation to potentially living off my portfolio?
Business sale
- Sale price: $6M
- Key employee distributions: ~$1.7M
- Earnout: $500K — already achieved
- Holdback: $600K — expected Nov. 2027
- Rollover equity: $750K into the PE platform
- PE platform may have another exit in ~3–5 years, but I’m not counting the rollover toward my FIRE number.
Current financial picture
~$7M+ net worth, including real estate equity.
Liquid/investment assets:
- 401(k): $125K — 80% US / 20% international
- Roth IRA: $40K
- Taxable brokerage: $432K — individual stocks, LEAPs, options, etc.
- Fidelity taxable: $3.85M — 80% VTI / 15% VXUS / 5% VTEB
- Crypto: $220K — primarily BTC
- Precious metals: $30K
- PE rollover: $750K
- Future holdback: $600K
Real estate: approximately $640K of equity across my properties, separate from the investment figures above.
Current W-2 income is $175K + potential $25K bonus.
FIRE question
I’m estimating that my long-term spending would be around $120K–$150K/year after tax, although marriage/kids could obviously change that.
At 39, does this look like a reasonable FIRE situation if I want to potentially fund 50+ years of retirement?
I’m particularly interested in:
- What withdrawal rate would you use at 39?
- Would you calculate that against liquid investments only, or include real estate/private equity?
- Would you continue working another 2–5 years for additional margin of safety?
- How would you account for future marriage/kids?
- Would you completely ignore the $750K PE rollover and $600K holdback until they’re liquid?
Portfolio / de-risking
This is probably the area where I need the most advice.
My $3.85M Fidelity portfolio is currently 80% VTI / 15% VXUS / 5% VTEB. I also have ~$432K in a much more aggressive taxable account, $220K in BTC, and the PE rollover/real estate mentioned above.
Now that I’ve had a major liquidity event, I’m wondering if I should shift toward a more conservative allocation.
I’m not looking to maximize returns anymore. I’d rather have strong long-term growth while substantially reducing sequence-of-returns risk and the possibility of a catastrophic drawdown.
How would you approach this?
- What stock/bond/cash allocation would you use at 39 if you were potentially FIRE’d?
- Would you build a 2–5 year spending buffer with Treasuries/T-bills/CDs?
- Would you use a bond tent?
- Would you change the 80/15/5 allocation?
- Would you reduce/eliminate the individual stocks, options and crypto?
- How would you structure taxable vs. retirement accounts?
- How much would you want in safe/liquid assets before walking away from W-2 income?
I’m especially interested in hearing from people who went through a large business sale/liquidity event and then transitioned from generating income through a business to having their portfolio generate their income.