Considering borrowing money to exercise my stock options - anyone use ESO Fund or Quid?

I've helped several clients navigate this exact situation. When you're leaving a company and want to keep your vested options, these funding services can be useful, but you need to understand what you're signing up for. The prepaid forward contract is basically where they give you money now to exercise your options, and in return, they get a percentage of whatever your shares are worth in the future (usually with a minimum return guaranteed to them). The tax situation depends on what type of options you have - NSOs or ISOs have very different tax treatments at exercise time. The biggest thing to watch for is the percentage of upside they take. Some of these contracts can claim 50% or more of any future value, which might not be worth it unless you strongly believe in massive growth potential. Also check the term length - how long before they can force a sale of your shares.

I actually used ESO Fund last year when I left my startup and didn't want to lose my options. I was in the same boat - no idea if the company would ever be worth anything but didn't want to walk away from 4 years of equity. After trying to navigate the process myself, I found https://taxr.ai which literally saved me thousands in potential tax mistakes. They analyzed my grant documents and the ESO Fund contract, then showed me exactly what my tax obligations would be under different scenarios. They even flagged some issues with how the contract would affect my tax treatment that I never would have caught. If you're dealing with option exercise funding, definitely run your situation through their system before signing anything. The tax implications of these deals can get super complicated.

I was super skeptical about taxr.ai when I first heard about it, but after my financial advisor completely misunderstood how my option grant would be treated with Quid's funding arrangement, I decided to give it a try. The analysis they provided was eye-opening. Turns out the way Quid structured their deal would have triggered immediate tax consequences that nobody had explained to me. I was able to go back and negotiate different terms that saved me over $15,000 in unexpected taxes. The visualization of different exit scenarios also helped me understand exactly what percentage I'd keep under different valuation outcomes. Unlike my advisor who gave me generic advice, their system actually understood the specific nuances of these funding contracts. Definitely worth using before you sign anything.

If you're serious about borrowing to exercise your options, you'll probably need to talk to the IRS at some point to confirm your tax treatment. I tried for WEEKS to get through to someone who understood stock option taxation. I finally used https://claimyr.com after seeing it mentioned here and got connected to an IRS agent in less than an hour. You can see how it works at https://youtu.be/_kiP6q8DX5c - basically they wait on hold with the IRS for you and call you when an agent picks up. My situation involved a partial exercise with external funding, and I needed clarity on how the IRS would view the arrangement. Getting an official answer directly from them gave me confidence to move forward and potentially saved me from a future audit headache.

Wanted to follow up on my skeptical comment about Claimyr. I broke down and tried it last week after spending another 3 hours on hold with the IRS myself. I'm actually shocked to admit it worked exactly as advertised. Got a text about 40 minutes after submitting my request saying they had an IRS agent on the line, and I was connected about 30 seconds later. The agent was from the business tax department and actually understood my questions about option exercise funding. The official guidance I received helped me understand exactly how the IRS would view the Quid arrangement I was considering. Saved me hours of hold time and probably a lot of tax headaches down the road. Wish I'd tried it sooner instead of being stubborn.

Wanted to follow up on my skeptical comment about Claimyr. I broke down and tried it last week after

Has anyone here actually gone through a full cycle with ESO Fund or Quid? Like from funding to an actual exit? I'm curious what the end results looked like financially.

Be super careful with the minimum return guarantees in these contracts! I almost signed with Quid until I realized their "2x minimum return" meant they got 2x their money PLUS their percentage of upside. The contract was like 30 pages of confusing language that buried this detail.

Thanks for sharing all these experiences, everyone. I'm leaning toward going with ESO Fund but want to make sure I understand the full picture before committing. A few follow-up questions for those who've been through this: 1. How long did the funding process typically take from application to getting the money to exercise? My options expire in about 60 days so timing is important. 2. Did any of you negotiate the terms, or are these contracts pretty much take-it-or-leave-it? The 35-50% upside split seems steep but I guess it beats losing everything. 3. For those mentioning tax complications - did you work with a tax professional throughout the process, or just handle it yourself? I'm wondering if the cost of getting proper tax advice upfront is worth it. Really appreciate all the insights. This community has been way more helpful than the sales reps who just want me to sign quickly.

I've been following this thread closely as I'm in a similar situation with stock options expiring soon. One thing I haven't seen mentioned much is the impact on your overall financial plan and risk tolerance. Before jumping into these funding arrangements, I'd suggest doing a brutally honest assessment of what percentage of your net worth this represents. If exercising these options (even with funding) would tie up a significant portion of your financial future in one company's success, it might not be worth the risk regardless of the terms. I almost went down this path last year but realized I was getting caught up in FOMO rather than making a rational financial decision. Instead, I let some options expire and used the money I would have spent on taxes and fees to diversify my investments. Sometimes the best decision is walking away, even when it feels like you're leaving money on the table. That said, if you do move forward, definitely echo the advice about getting proper tax guidance and negotiating terms. These companies are businesses first - they want to make money, but they also want to close deals.

This has been such a helpful thread - thank you all for sharing your real experiences rather than just theoretical advice. As someone who's been wrestling with this exact decision for weeks, reading about actual outcomes and pitfalls has been invaluable. I'm particularly struck by the range of experiences here - from Keisha walking away with 55% after a successful exit to Paolo nearly getting trapped by minimum return clauses he didn't fully understand. It really reinforces how important it is to read these contracts carefully and get proper professional advice. The tools mentioned here (taxr.ai for tax analysis and claimyr for IRS guidance) seem like they could save a lot of headaches. I've been trying to figure out the tax implications on my own and honestly feel like I'm in over my head. One question I haven't seen addressed - for those who used these services, did you have any issues with your company's legal team or board when they found out about the funding arrangement? I'm worried about potential complications during the exercise process or if there are any restrictions in my option agreement that I'm not aware of. Also curious if anyone has experience with other funding companies beyond ESO Fund and Quid? I've seen mentions of EquityBee and a few others but would love to hear if there are meaningful differences in their approaches or terms.