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Biggest career decision of my life this week (1 Viewer)

Judge Smails

Footballguy
I'm 52 and only have so many prime earning years left. Critical decision as I don't have time to make up for wrong moves.

Considering walking away from a ton of equity with my current job for one that is recruiting me with a lot higher base (maybe $100K more), a lot higher (2+X) W2 but much lesser equity.

Have to make the decision by next weekend. I can hardly sleep. More due diligence the next several days. Lots of other factors. I can't F this up.

 
Second paragraph was gibberish to me.

If you are in good health then you may havebmore earning years in you than you think. If not you may want to take the fast money. Go with your gut about how you feel you can maximize your money

 
I've been a career salaryman. What's the potential impact of the equity? Do you own a piece of the company? If so, how does cashing it in work?

 
I've been a career salaryman. What's the potential impact of the equity? Do you own a piece of the company? If so, how does cashing it in work?
Yeah, how can you cash it in? Is it only upon a change of control or liquidation event? Sounds like it's restricted.

 
Equity is great but are you walking away from value or just potential value at some uncertain future date?

 
Cash is King
depends...if given equity in the right situations it can DWARF the extra $50-$100k salary and truly make you a fortune. It all depends on the underlying company, it's strength / profitability as well as the timeframe / restrictions to cash out. The fact that he's considering walking away from the equity it doesn't sound like there's a million + potential gold mine potential.

 
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Depends on many factors for me as I have these decisions periodically.

- How liquid is the equity? Private companies with little chance of going public in the next 10 years can have equity that you can't cash in on. I had a CEO who, when I was considering a new role and looking at taking some compensation in stock, told me "Always take the cash. Cash is king". Turns out, I could have wiped my ### with the stock about 5 years later.

- Where are you in your family life? I took less money where I am so that I can be there most of the time to see my kids grow up (coach sports, tuck them in at night, do things with them, etc.). You don't get to do that part of your life over either

- What are the risks if things don't work out? At your age, it could be tough to get another job if things don't work out.

- Are you looking for more out of this new opportunity than money? I am not one to just chase money. If you are going to be putting in more time and increasing your risk, you really better love that job and have opportunity to be there for a little while

 
I'm younger so I can handle the risk for more equity, but at 52, the difference over the next 7-8 years of $100k is obviously around 3/4 million - An extra chunk of real cash for retirement sounds enticing if I was in that situation. I also assume you already have some vested equity at your current position.

Good luck!!

 
I'm younger so I can handle the risk for more equity, but at 52, the difference over the next 7-8 years of $100k is obviously around 3/4 million - An extra chunk of real cash for retirement sounds enticing if I was in that situation. I also assume you already have some vested equity at your current position.

Good luck!!
Pretty sure from a prior thread that he forfeits even the vested equity (or at least all of the upside value) if he leaves.

 
I'm 52 and only have so many prime earning years left. Critical decision as I don't have time to make up for wrong moves.

Considering walking away from a ton of equity with my current job for one that is recruiting me with a lot higher base (maybe $100K more), a lot higher (2+X) W2 but much lesser equity.

Have to make the decision by next weekend. I can hardly sleep. More due diligence the next several days. Lots of other factors. I can't F this up.
does this mean you'd lose all of the equity you have or you just stand to gain more if you stay?

If it's giving up what you have, it sounds similar to my peer group at work, five years away from a very nice pension yet we still find people voluntarily leaving for slightly higher salaries. (many involuntary too, but that's different)

You need to assess where you're likely to be in 5, 10, 20 years. Satisfaction, worst case scenario, best case, etc.

 
I'm 52 and only have so many prime earning years left. Critical decision as I don't have time to make up for wrong moves.

Considering walking away from a ton of equity with my current job for one that is recruiting me with a lot higher base (maybe $100K more), a lot higher (2+X) W2 but much lesser equity.

Have to make the decision by next weekend. I can hardly sleep. More due diligence the next several days. Lots of other factors. I can't F this up.
We're the exact same age and I'm in a similar position, but we're probably closer to a successful exit as a company so it's easier to justify staying the course. 12 years ago I walked away from a large equity stake because I didn't want to true up my position when we had 1:20 reverse split after our 12th M&A in 5 years - I would have had to write a check for $75K to maintain my pro rata share in the cap table. Missed out on a having a significant piece of a $100M exit that came 3 years later. Right now I stand to have a 7 figure payout at the right sale. At the wrong sale price? Well, debt comes before equity. I don't sleep very well these days.

GLGB

 
Grass is greener theory.

I've seen all too many people make what they thought was going to be a great move upward that a company was promising only to see people ultimately regret the move because Mr. New Company wasn't telling the entire story.

My vote is stay and don't look back.

 
I'm 52 and only have so many prime earning years left. Critical decision as I don't have time to make up for wrong moves.

Considering walking away from a ton of equity with my current job for one that is recruiting me with a lot higher base (maybe $100K more), a lot higher (2+X) W2 but much lesser equity.

Have to make the decision by next weekend. I can hardly sleep. More due diligence the next several days. Lots of other factors. I can't F this up.
We're the exact same age and I'm in a similar position, but we're probably closer to a successful exit as a company so it's easier to justify staying the course. 12 years ago I walked away from a large equity stake because I didn't want to true up my position when we had 1:20 reverse split after our 12th M&A in 5 years - I would have had to write a check for $75K to maintain my pro rata share in the cap table. Missed out on a having a significant piece of a $100M exit that came 3 years later. Right now I stand to have a 7 figure payout at the right sale. At the wrong sale price? Well, debt comes before equity. I don't sleep very well these days.

GLGB
I didn't fully understand this, but it sounds like a bad beat

 
I felt the same way about 10 years ago. At the time, I was making about $10 an hour and had the chance to get $14 an hour at another company, but I didn't know if the "fit" was right. I couldn't sleep for days. What a rough time in my life.

 
You should be able to make some solid estimates of the value of the equity in your current role. Give it a +/- 10% (or more if you think your company's position is volatile or at risk) and compare the NPV of the two over however long you plan to stay working.

Unless there is a huge disparity make your decision based on what job you think will deliver the best quality of life. I'd say we're all in our prime living years, regardless of how old we are. Don't give up 7-10 years to a job that will make you less happy now if the difference in long-term security for your family isn't dramatically improved.

 
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I'm 52 and only have so many prime earning years left. Critical decision as I don't have time to make up for wrong moves.

Considering walking away from a ton of equity with my current job for one that is recruiting me with a lot higher base (maybe $100K more), a lot higher (2+X) W2 but much lesser equity.

Have to make the decision by next weekend. I can hardly sleep. More due diligence the next several days. Lots of other factors. I can't F this up.
We're the exact same age and I'm in a similar position, but we're probably closer to a successful exit as a company so it's easier to justify staying the course. 12 years ago I walked away from a large equity stake because I didn't want to true up my position when we had 1:20 reverse split after our 12th M&A in 5 years - I would have had to write a check for $75K to maintain my pro rata share in the cap table. Missed out on a having a significant piece of a $100M exit that came 3 years later. Right now I stand to have a 7 figure payout at the right sale. At the wrong sale price? Well, debt comes before equity. I don't sleep very well these days.

GLGB
I didn't fully understand this, but it sounds like a bad beat
More like folded an open ended draw to a big raise.

 
Let me put this in my terms; you're here hostile takeover but you didn't count on this poison pill running around. But I can help you, I'm your white knight!

 
I'm confident you'll think it through, consult with your trusted advisors and make the right call. Good luck Judge.

 
I'm 52 and only have so many prime earning years left. Critical decision as I don't have time to make up for wrong moves.

Considering walking away from a ton of equity with my current job for one that is recruiting me with a lot higher base (maybe $100K more), a lot higher (2+X) W2 but much lesser equity.

Have to make the decision by next weekend. I can hardly sleep. More due diligence the next several days. Lots of other factors. I can't F this up.
I thought you were a judge?

 
I'm 52 and only have so many prime earning years left. Critical decision as I don't have time to make up for wrong moves.

Considering walking away from a ton of equity with my current job for one that is recruiting me with a lot higher base (maybe $100K more), a lot higher (2+X) W2 but much lesser equity.

Have to make the decision by next weekend. I can hardly sleep. More due diligence the next several days. Lots of other factors. I can't F this up.
I thought you were a judge?
I think that's in the chili making contest.

 
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This is not something to stress about. You are either going to be wealthy or wealthier. Better off than 99.999% of people in the history of the world.

Enjoy the process, man.

 
I've been a career salaryman. What's the potential impact of the equity? Do you own a piece of the company? If so, how does cashing it in work?
Yeah, how can you cash it in? Is it only upon a change of control or liquidation event? Sounds like it's restricted.
It is. Either we got bought or IPO. 400K shares at 20 cents. Almost 1/2 percent of the company. Bought with promissory note so it would be capital gains. Could be worth a couple hundred K to north of $2M (when we dream of the crazy valuations out there). Private equity company is 2 years in and they normally like to flip in 3-5 years. My issue? for a software company we suck at building software. We keep selling but losing customers. I think our shine is off as an acquisition target, even with growth. Maybe I'm wrong though. Talking prepping for an IPO, but this is no sure thing. I keep asking myself - would I buy stock in our company? I'm struggling big time.
 
I'm younger so I can handle the risk for more equity, but at 52, the difference over the next 7-8 years of $100k is obviously around 3/4 million - An extra chunk of real cash for retirement sounds enticing if I was in that situation. I also assume you already have some vested equity at your current position.

Good luck!!
Pretty sure from a prior thread that he forfeits even the vested equity (or at least all of the upside value) if he leaves.
Correct. Best case is I realize a pittance (likely not 6 figures) from a new higher valuation. But possibly nothing. But I could stay 10 years, get fired, leave or die and if there is no liquidity even while I'm with the company I get nothing.
 
I'm 52 and only have so many prime earning years left. Critical decision as I don't have time to make up for wrong moves.

Considering walking away from a ton of equity with my current job for one that is recruiting me with a lot higher base (maybe $100K more), a lot higher (2+X) W2 but much lesser equity.

Have to make the decision by next weekend. I can hardly sleep. More due diligence the next several days. Lots of other factors. I can't F this up.
:shark:

 
More factors in the decision:

Current company:

Pros - love the CEO and team, potential equity, sorta sexy story to tell in the market. Work from home when not traveling - a big factor considering I live in So Cal. Earned high degree of freedom. I work hard but I can also do pretty much what I want to do (start at 6am, go to gym at 4, have dinner, get back to work, mix in some golf once in awhile, etc). SVP title over sales of all of NA. Took me awhile to get there so getting lots of offers for similar positions.

Cons - overpromise and under-deliver. Getting bad reputation in the market and customer churn is frightening. Weak engineering team but getting better. Benefits aren't great, especially health plan. Even top performers in sales management or executive leadership NEVER hit at plan compensation. Best is maybe 80%. There is such a drive for high growth so we can exit that the #'s in the plan are not realistic. They get downgraded for the company mid year - but not in our comp plans. So we always fall short of at plan comp targets. Company bonuses hit the last 2 quarters but missed the previous 8. Morale is fragile. Losing deals a lot more than in the past due to reputation catching up to us (as well as competitors). The code is out of my control. That's my biggest frustration. Equity cashout is not guaranteed. Could disappear. CFO was replaced and I know the guy sent packing got zip.

New suitor:

Pros - explosive growth. We're talking 70 percent last year. Highly rated products. Said they won every major deal they went after last year. CEO and EVP said to be great, approachable at all levels of the company, etc. CEO and company HQ out of the country. Truly international company in the UK, Australia, etc. Winning important National Health IT business. Only skyped with the CEO, but great guy, wants winners on the team that can help grow the business and he can also have a beer with. Big increase in cash comp. We're talking up to 100K in base and potentially 1.5-2X of W2 based on what people in the same position have done (including the EVP who was in the role previously). Great benefits - including current 100% paid premiums for PPO for entire family, with 750-1500 deductible. Beautiful office right off PCH, ocean views.

Cons: Even though they are rumored to be likely going the IPO route, they are saying shares are locked up this year. I'd obviously like to have them in hand now before an event (even with longer vesting schedule) as opposed to getting them after the fact. Should be one of their bigger recruiting tools but they seem reluctant, saying they have never offered to new candidates before. I've been pressing - we'll see if it ends up in the offer letter. Commute - looks like if not on the road the expectation is you will be in the office. I've been a home office guy for 20+ years, even though I travel to corporate often. Still, I realize the higher up I go the expectation is they want you to be in the office. I've only commuted one time in my life and it was hell. This would be a much "prettier" drive looking at the Pacific, but it's still 50 minutes with no traffic and an hour and a half if gets backed up. Don't know if I could deal with 2-3 hours every day. On the flip side I wouldn't have to relocate - which his big. Even though the comp is much higher the title looks like a drop. Going from an SVP over the whole country to a VP over top National Accounts. Still manage the same team size, but on paper from a career perspective it would look to be a downward move.

Summary - to Dentist's comments I'm FULLY aware the grass is not always greener. Many times it isn't. I'm going to look at this from a happiness/quality of life perspective as much as I am $$. But right or wrong, I do look at this differently at 52 then I would at 42. At 42 I would just ride the shares because I have time. But if ride this for 3-5 years and the shares don't pay off it would suck and not as much time to take another successful shot before I want to be spending a lot more time making chili, golfing and in Cabo :D

 
I felt the same way about 10 years ago. At the time, I was making about $10 an hour and had the chance to get $14 an hour at another company, but I didn't know if the "fit" was right. I couldn't sleep for days. What a rough time in my life.
What was it about the other position that you were unsure about?

 
Based on what you say about QOL at your present job, make sure you get a damned good feel for the CULTURE of the suitor firm. I remember back when I was with The Firm, I got courted away with enticements similar as yours. During the interview process, I noted a couple of "red flags" that I improperly dismissed. After I joined the new outfit, it didn't take long to realize the culture... their way of doing things and mine... were just incompatible. I stuck it out six months... got a great review after that, then called my old boss at The Firm and confessed I made a mistake. He hired me back on the spot.

Today, all the people with whom I work are ex-Firm employees... the culture of our workplace is the same as what I was used to.

So that's something else to think about. It's cliche because it's true... but old dogs really don't learn new tricks very easily.

 
Can you not go back to your current employer and tell them you have a better offer? Are you expendable? Would they match (or at least shrink the comp gap)?

Im 40 and I think about leaving all the time but for me it always comes down to culture. Im happy at my job and couldnt risk it for more money elsewhere unless I knew Id be equally content.

As for driving an hour each way everyday, no friggen way:)

 
Tough call. If you are noticing the decline in your current company, chances are others are too. It sounds like it might be a good time to exit.

And I generally agree with the "take the cash in hand" sentiment. Lots of people get screwed by options that never really materialize. You are taking about a nice bump in your base, and that's hard to pass up.

Good luck!

 
I felt the same way about 10 years ago. At the time, I was making about $10 an hour and had the chance to get $14 an hour at another company, but I didn't know if the "fit" was right. I couldn't sleep for days. What a rough time in my life.
You sure you're a FBG?

 
I've been a career salaryman. What's the potential impact of the equity? Do you own a piece of the company? If so, how does cashing it in work?
Yeah, how can you cash it in? Is it only upon a change of control or liquidation event? Sounds like it's restricted.
It is. Either we got bought or IPO. 400K shares at 20 cents. Almost 1/2 percent of the company. Bought with promissory note so it would be capital gains. Could be worth a couple hundred K to north of $2M (when we dream of the crazy valuations out there). Private equity company is 2 years in and they normally like to flip in 3-5 years. My issue? for a software company we suck at building software. We keep selling but losing customers. I think our shine is off as an acquisition target, even with growth. Maybe I'm wrong though. Talking prepping for an IPO, but this is no sure thing. I keep asking myself - would I buy stock in our company? I'm struggling big time.
you just made your case right here. Cash is king....get out.

 
Current job:

Work from home when not traveling - a big factor considering I live in So Cal.
Potential job:

I've only commuted one time in my life and it was hell. This would be a much "prettier" drive looking at the Pacific, but it's still 50 minutes with no traffic and an hour and a half if gets backed up.
You're insane to be considering this.

 
GL Smails.

on the home office/commute issue, don't make light of it. it's not as important as some of the other considerations, but you still have to think about how it will affect you, both on the job and in your home life. a couple years ago working for a consulting company, I spent 2.5-3 hours a day on the road after spending 20 minutes or less for many years. the worst part is that it wasn't that far, only from the west valley down to Wilshire & back. but it still took 1-1.5 hours each way. by the time I got home every day, I was so miserable that I didn't want to do anything. the SoCal traffic will beat you down.

if you commute an average of 2 hours a day, that's 1 month out of every year that you'll be on the road for work.

:2cents:

 
Current job:

Work from home when not traveling - a big factor considering I live in So Cal.
Potential job:
I've only commuted one time in my life and it was hell. This would be a much "prettier" drive looking at the Pacific, but it's still 50 minutes with no traffic and an hour and a half if gets backed up.
You're insane to be considering this.
Totally agree this is a pretty decent consideration.I have a job where I'm commuting about half the time with a pretty similar drive and it sucks bad.

Sounds like you have great options either way so you have been doing something right. Congrats on that and good luck.

 
All else being equal, the extra money could make the one time cost of a move to a location closer to the new job worth while, if you've got equity in your current house of course.

 

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