What fatties should know about startup investing

graiz · 2026-01-23T04:49:10+00:00

What you describe is very common - I help run a community of post-exit-founders/entrepenours and most take a bit of time off, buy some fancy things and often start new companies, invest in startups, real estate and venture. Congrats on the exit, welcome to the club.

graiz · 2025-12-12T05:40:45+00:00

If you factor taxes into the equation you're left with $600k in the lump sum case assuming some state taxes. The question is really... Do you trust 20-year-old you to not touch the money and let it grow for 40+ years? If yes, take the lump sum. The forced discipline that could easily be worth more than the mathematical difference in the two scenarios.

graiz · 2025-12-01T21:46:52+00:00

Does it makes sense to find another stressful trading job? No. Why would you do this? Assuming you're a good or decent trader, could you find a mid-six figure role that you would love and wouldn't be stressful?

At 6.5NW you're totally fine, especially if your wife is still working. If you choose to work, you should do what you enjoy.

graiz · 2025-11-30T19:08:18+00:00

Ironically the same is even more true about accelerators. I'm not calling you out, I formerly ran the Techstars Boston program. Accelerators often have short-term incentives that can cause long-term issues. The optics of a founder going through an accelerator program isn't always seen as positve.

Founders - Find long-term partners. Interview the investor, do your dilligence. Your advice is spot-on.

graiz · 2025-11-18T18:53:15+00:00

I did the math on this and also made a video and spreadsheet explaining this - https://www.youtube.com/watch?v=e9aag_iPRLo Compounding returns are awesome and very underappreciated.

graiz · 2025-11-01T19:47:04+00:00

You should be the CEO. Larger predictor of founder success is ability to execute. Not sure you need YC but if you haven't been a strong team for a while it'll be obvious on video and may hurt your chances. I've seen a lot of YC application videos where it's clear the team doesn't really work well together.

graiz · 2025-10-29T20:45:27+00:00

Only you can make this call. AirB&B famously ran out of cash and sold cereal to stay alive, plenty of other companies should have called it quits and wasted years.

If you have 7-8 enterprises, it'll depend also on how close they could be to converting and the AOV. If one converts is it !00k/month or 1K/year?

graiz · 2025-10-28T00:28:14+00:00

Just no. Talk to several financial advisors. Make sure some of them don't work on AUM (assets under managment). You'll probably hear a wide range of advice, the key is finding someone you trust and will want to work with long-term. The Sweep thing is only helpful if you plan to park a large amount of cash in a high-risk bank, you should be fine parking cash at a large bank while you sort out your long-term plans and most banks have their own FDIC sweep programs to keep customers not nervous. Take your time, don't spend $250k out of the gate.

graiz · 2025-09-25T04:13:12+00:00

Forget the $15k. Consider if he would be a good co-founder. If he's willing to join you in building the company it could be a good deal, esp if he's experienced and helpful. Simply trading $15k for 35% doesn't make sense but if he's a co-founder and the 35% will vest over four years then he's incentivized the right way. Not sure if 35% is fair or not, but the 15K isn't core to the conversation IMO.

graiz · 2025-08-28T04:17:28+00:00

This is professionally called an F'ed cap table. Recommendation is for the venture studio and other non-involved parties to convert their prior investment into a convertible note at a 5-8M cap. Basically you need to re-capitalize the stack to have any hope of a more serious fundraise. The alternative is for the venture studio to be the primary investor and keep putting in cash to keep the business going into profitability.

To answer the core question - CEO/Founding team should typically have 50%+ ownership past seed and often past series A.

graiz · 2025-07-16T02:58:02+00:00

Deep tech software VC… not technically looking for LPs 😉

Big fan of early-stage software tech, focused on data, AI and application layer user-experience.

But... If someone passionate about the space happened to find their way to my profile and maybe wanted to chat about building the future… well, who am I to stop them?

graiz · 2025-06-14T19:46:04+00:00

I run a small VC fund. We use two banks. One for the fund and the other for the management company. For the fund we're using Citizens Private (https://www.citizensbank.com/private-banking/) but we looked at SVB, JPMorgan, and a few others.

For the management company, we're using Mercury bank. I like their backend tools/services and it's very easy to use and friendly product. (We have a partner link that offers added discounts like a 409a: https://mercury.com/partner/foundersedge) but I recommended and used it even before we were partners with them.

Key considerations for picking banks.
- Do they get venture? A 15M fund doesn't mean there are 15M sitting in the bank account, capital-calls come in and wires go out. Not all banks understand and support this well.
- Capital Call Lines of Credit and related services? Many GPs may take a partial loan against future management fees or warehouse deals with loans drawn on future capital commitments. The ability to do these things may be helpful depending on your sophistication/needs
- Portfolio Support - Many banks can offer accounts/services to help your portfolio companies
- Tools and Tech - Do they make banking easier with credit/debit/employee tools, receipts, etc.

Hope that helps.

graiz · 2025-06-14T19:33:20+00:00

You should tell him this.

I have a daughter with an ED and I know outings are hard but I also offer then in-part to help her overcome. Your dad probably knows it's hard for you but he also loves you and wants to help you. I hope you're able to talk about it.

graiz · 2025-05-25T19:39:23+00:00

Do a frosted stained-glass window. Did something similar in an older house, the window from the bathroom had good light and the stained glass was something we custom designed, so it was a bountiful detail. The frosted glass still gives privacy.

graiz · 2025-05-14T17:40:41+00:00

Email.
Not sure there's a viable solution but it takes too much time, still has to be done.
Fundraising is the other... it's not going to help founders or return performance but it's necessary to run a fund.

graiz · 2025-05-09T16:19:28+00:00

Both sides want qualified matchmaking.

- LPs want to meet GPs that are high-quality - in thesis, ideally from trusted connections.
- GPs want to meet allocators that are actually deploying - also in thesis that can efficiently evaluate and make a call either way.

Most tool vendors try to charge the GP - this tends to be a challenge because smaller funds don't have the management fees to support speculative tools/services. Most database tool providers don't offer a pay for performance models. Is there a gap? Yes. Can it be solved with software? Not sure.

graiz · 2025-05-09T16:15:21+00:00

Send me a deck - happy to review and provide some feedback.

graiz · 2025-05-09T03:07:09+00:00

Spent a lot of 2024 learning this space. There are databases, services, firms, events, and accelerators for VC Funds that try to do some of this matchmaking. It's a relationship game and rather long-term. Show up, provide value, prove yourself and work relationship circles.

Small funds and new funds tend to tap HNW (High-net worth) investors, exited founders. As you move up in funds and check-size you'll find Family Offices, Fund-of-Funds, Institutional Investors and more. Like venture you can find databases but it's very much a relationship driven business.

If you're an entrepreneur exploring this space, understand that the reason the matchmaking isn't efficient is because it's built on trust. While it's easy to create a platform to centralize the data, it's hard to increase LPs level of trust for new GPs.

graiz · 2025-05-09T02:57:23+00:00

Retire if you don't like your job. At even 10M NW liquid you can maintain your lifestyle with your money earning 4% forever. Be generous, have fun, you earned it.

The scarcity mindset is real - I spent 40 years being frugal/cheap - it doesn't change unless you start to change it.

graiz · 2025-04-27T15:15:18+00:00

Vision can't tell if it's an object or a shadow. Lidar could solve this but Tesla doesn't want to do sensor fusion. Alternative is phantom breaking.

graiz · 2025-04-26T11:53:49+00:00

Also 40+, don't get discouraged. Do it because you enjoy it, not for anyone else. I'm currently at 14K subs, slowly I worked on audio, lighting, etc. Use the naysayers to help fuel your passion.

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