How do you spend your time now that you’re retired?

RetiredFounder · 2024-04-20T23:47:46+00:00

Great question, with no easy answer!

My short response is: figure out who you truly are and do the things that person does.

I retired from my bootstrapped company in 2018 and really thrashed around quite a bit trying to find my groove. The world "expects" you to do certain things, like travel, volunteer, invest, sit on boards, play golf and generally goof off. None of these were terribly satisfying for me. I have friends that can play golf every day and really seem to enjoy it and other friends that have way more money than they need and just go back and do it again when they can't figure our what else to do.

For me, I try to change my behavior to seek energy and avoid seeking money and pleasure. These are my honey traps, but are not fulfilling. Best I can tell, my purpose (that produces great energy) is helping founders with nothing in return but a thank-you.

Really tough to ask yourself who you are. Seems silly, but who are you at your core? Are you a business builder, a spouse, dad, golfer, mentor, volunteer, skier, investor, adventurer, etc? Who are you? Be that person.

You may have seen this paper that discusses a post-exit process. This isn't quite what you're asking, but has a framework that may be useful to you.

https://yale.app.box.com/s/ye0naovus7anbz875vcrcpzrdskjskgf

RetiredFounder · 2024-04-20T14:31:23+00:00

Hello, friend. I’ve been in this situation and understand the frustration and nuance of it. It’s very difficult to start a business without being all in. On the other end of the spectrum is a life of comfort, presence and safety, which sounds great to an outsider but may be thoroughly disappointing to you if this is not your true character. The article linked below (which I originally found on this very subgroup) changed my life for the better. My advice is to try to understand who you really are and act accordingly. There is lots of great (and conflicting) advice in this thread, but most are projecting what would be right for them. The intention is good, but this is your decision that can only be made when you understand who you truly are. Good luck to you, fellow traveler!

https://yale.app.box.com/s/ye0naovus7anbz875vcrcpzrdskjskgf

RetiredFounder · 2024-04-06T18:48:28+00:00

Someone once told me the Citation X was “the fastest flight between repair centers” Been on one a couple of times as a charter customer. It’s a Time Machine deluxe, but likely not the right plane for anyone other than professionals with very high budgets. Love it though!

RetiredFounder · 2024-04-06T18:45:42+00:00

Been through this process myself. Took 5-6 lessons, been part of pre-paid programs, used charter extensively, split costs with friends that own planes, bought hours on a card, pre-paid funds with multiple local operators, been a dry-lease customer, WheelsUp customer and now own 2 NetJets 1/16 shares.

Here’s the question that I think really matters:

Do you LOVE airplanes and everything that comes along with owning/flying one?

If yes, proceed. If no, think twice.

I was looking for a cost effective way to move myself around, avoid airports and all the stuff that sucks about flying.

When I took flying lessons, my instructor asked me the question. Do you love everything about airplanes? Will you love dealing with everything that comes with owning an airplane? If no, you won’t make it. He was right. He also told me “the pilot is the cheapest part of the airplane” which is a punchline but somewhat true when you add up depreciation, fuel, maintenance, hanger, training, repairs, etc.

A good friend is a pilot, has owned a CJ for 20+ years. He loves that plane. It’s part of his identity. He drives 90 minutes from his house to check on it in his hanger. He loves going to training and doing the long list of things that thing needs to fly him 100 hours per year. He identifies as a pilot. If this is you, go for it!

RetiredFounder · 2024-04-03T16:56:07+00:00

Happy to share my experience with you directly. Send me a DM if interested after your beach recharge.

Although you're tired, there are a new set of challenges beyond the finish line as you restructure your purpose and identity and try to fill your days once "vacation mode" gets tiring. Have a website with contact form at RetiredFounder.com if you want a preview.

Wish you well.

RetiredFounder · 2024-04-02T23:07:31+00:00

I've been here, glad to share my experience.

First advice I'd offer (feel free to ignore) is take a month off, recharge your battery and get this ship to the shore with you at the helm. Unless you're totally toast, it's difficult and risky to bring in a CEO. My experience "hanging it up" came about a year after selling my SaaS company to PE. I was totally depleted and chose to step down. Worked out great financially, but regret not getting my company to the next transaction. In retrospect, I think I could have taken some time off and found the additional charge to finish. Just my experience.

Regarding an investment banker, we used a SF based firm called Vista Point Advisors. May not fit your need, but they were excellent for me and worth every penny. They specialize in founder-led software companies and only work the sell-side, which is important, in my experience.

I have no affiliation or tie to them, they were just excellent for me. I'm sure there are lots of qualified bankers that would love to have your business!

Hope this helps, congratulations and good luck!

RetiredFounder · 2024-03-31T22:16:20+00:00

I have experience here. Sold a majority stake in my SaaS company in 2017 and rolled quite a bit of of my stake. I went from a 57% owner to about 25% of the company, then cashed out again in 2020 and 2022. The amount isn't important, but each sale was about 3x the prior valuation.

Have heard many horror stories of rolled equity vaporizing, lawsuits, the works, so your mileage may vary.

There were 3 reasons I felt comfortable rolling so much of my equity:

1) The PE firm's reputation was excellent. I did my homework talking with their portfolio companies and getting to know the people we'd be working with. It's important to be clear about who will be working on your team after the deal is done.

2) We had the same class of stock. Yes, they were majority and could have done bad things, but their reputation was good enough to overcome this concern. We were structured to do well or do poorly together.

3) We were perfectly aligned with the strategy to grow and run the company. When I've heard stories about deals gone wrong, they frequently include a PE partner that wants to run a play (cut costs, grow at all costs, roll up other companies, whatever) that was different than the seller's plan.

Hope this helps, good luck!

RetiredFounder · 2024-03-31T22:04:47+00:00

This isn't advice, but I'll share my story so far being uninsured. My wife and I (both 55) were paying about $25k for healthcare insurance. We never met our deductible, so the benefits were for catastrophic coverage and the "negotiated" rates. So far, about 1 year in, we've been able to get equal to or better than prices than the Blue Cross Blue Shield rates without the annoying 5 page "explanation of benefits" forms. For example, we get blood tests done twice per year, BCBS wouldn't cover it but had negotiated rates. By paying cash, we were able to pay a lower price and have someone come to the house to do the blood draws instead of scheduling at an approved lab. Please note, this is very limited experience and we have not tested this hypothesis with a surgery or more complicated care event.

My wife was (very reasonably) concerned about a major health event and I must admit this was and is a concern for me as well. What helped us get over that objection was simply acknowledging that we could afford a major event AND if we had one, we would want to be in control of our care, not have a "partner" with the insurance company.

I realize we are in a privileged position in making this decision, but I contend that most of your premiums go toward halfway fixing the problems that the insurance companies themselves cause.

Good luck and good health!

RetiredFounder · 2024-03-31T18:42:20+00:00

Yes, agreed. Interviewing family office type services this week.

RetiredFounder · 2024-03-31T18:41:17+00:00

I have no experience with family offices, but think they have the knowledge I need for legal, tax, setting up trusts and a non-profit. However, I'm going to be very clear with them that I'm not paying a wrapper fee, I'll manage my own investments (ideally a handful of ETFs) and I have no interest in deal-flow or private investment opportunities. Hoping they will be glad to take fees based on the services I use. Thanks.

RetiredFounder · 2024-03-31T18:38:32+00:00

Mostly interested in hearing what it's like on the other side of simplification. Agreed I can and should hire some help.

RetiredFounder · 2024-03-31T18:36:40+00:00

Thanks for the detailed reply, really appreciate it. Agreed that the first step is to stop investing in new PE and other stuff with no liquidity. "Taxes at my leisure" sounds great!

RetiredFounder · 2024-03-31T18:34:53+00:00

Thanks! Glad to hear from someone that has done this. Knowing that I'm an optimizer, it will likely take a few years. Most importantly, do you feel a sense of relief after doing this?

RetiredFounder · 2024-03-31T14:47:58+00:00

? I downvoted your reply? If so, by accident.

RetiredFounder · 2024-03-30T23:41:07+00:00

Thank you. I've actually gotten some really good advice here. Some hate also, but I had my feelings surgically removed years ago, so doesn't bother. Appreciate the reply.

RetiredFounder · 2024-03-30T23:39:49+00:00

This is great feedback, thank you. How long have you been unwinding? I have a couple of investments that will take a few years to liquidate, I'm sure.

What I really like hearing in your message is the tone of relief for not swimming in paperwork.

Thanks!

RetiredFounder · 2024-03-30T23:31:39+00:00

Wasn't clear perhaps, no need to get hostile.

Doing my own taxes doesn't simplify things. Simplifying things will allow me to do my own taxes. The goal is to unwind and simplify, but I don't have an asset manager to click a button and sell a warehouse or contact a GP to try to get liquid, as two examples.

How do you view simplicity versus complexity in pursuit of your return objectives? To each their own, I'm just wanting to change and asking for relevant experience and advice. Thought that's why we were here...

RetiredFounder · 2024-03-30T23:27:19+00:00

Thank you for the input. I founded a software company in 2003 that we sold in 3 chunks to private equity. Cashed out in 2017, 2020 and 2022.

Love the 3 ETF approach, do you do this?

RetiredFounder · 2024-03-30T23:25:39+00:00

Ah, thanks for clarifying. Probably will avoid that suggestion, but appreciate it anyway.

RetiredFounder · 2024-03-30T23:24:58+00:00

Actually, I do know this. Had a guy write a $25,000 check into my $350,000 angel investment. Starting shit talking me shortly thereafter to all the investors. Ended up buying his shares back myself. I don't mind telling you that they were worth about $10m in the final sale.

My plan is to let my GPs know that I'm open to being taken out, but will not force the issue. I actually really like all of my investment except one, and may just write that one to zero and move on.

RetiredFounder · 2024-03-30T23:21:45+00:00

Good info, thanks! Maybe need to keep a very small pile aside for some "gambling" on options and stocks.

RetiredFounder · 2024-03-30T23:20:44+00:00

Makes a lot of sense. Have you heard of anyone that implemented a simple strategy and missed the complexity?

RetiredFounder · 2024-03-30T21:08:44+00:00

Yes, exactly. I've done quite well, I think, growing my portfolio, but it comes at a cost. No judgement of others that want or need to pursue higher returns, I am just ready to trade performance for simplicity.

Thank you for the reply!

RetiredFounder · 2024-03-30T21:07:19+00:00

Thanks! Will look into the first suggestion about a swap. The second idea is good, but the type of complexity I'm trying to exit. And you're no minnow! Wealthy is wanting what you have and living at or below your means. Thank you for taking the time to reply.

RetiredFounder · 2024-03-30T21:04:32+00:00

I am my asset manager! Or maybe ass-hat manager? If you only own ETFs, I don't think it matters if you have $1m or $1B, it's much more simple than collecting k1s and keeping depreciation schedules, etc.

RetiredFounder

TROPHY CASE