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ESPP & Matching retirement plan

Would you rather work at a start up where everything is constantly moving, possibly getting fat commission checks, or would you rather work at an established company with matching 401k plans and ESPP?


I'm asking bc my leadership at my startup thinks those benefits are over rated.

Would you rather...
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17
paddy
WR Officer
+11
Account Executive
Depends on your age and where you're at in life. If I'm young with no family/kids dependent on me, I'd take the risk at the smaller company since you have less to lose. If you have dependents and you're getting older, I'd go with the safer route at the established company.
aiko
Politicker
+9
Sr. Account Executive
I am young (ish) with no kids. I'm looking for a house in the bay area and I need steady income for my mortgage. I want kids in the next 1-2 years. Maybe going for the solid benefits will help me prepare for the next few years?
funcoupons
WR Officer
+12
that's queen coups to u
I think if you're wanting to settle down and start a family in the next few years, a more established company is a better fit. Most startups fail. For the ones that do survive, it's often feast or famine for several years while they stabilize themselves. Not ideal if you have a mortgage to pay and kids to feed unless you have a cushion of savings.
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Justatitle
Politicker
+11
Mid Market AE
Here’s the thing, benefits will pay off 25-30 years from now with a 401k and such but if you’re young and want to build your own portfolio from making a bunch of sales in a startup then go for it. Realize risk and mitigate it as best possible
aiko
Politicker
+9
Sr. Account Executive
Thank you! I'm all about planning for the future and my current startup isn't moving fast enough 😩
Justatitle
Politicker
+11
Mid Market AE
Yup and they probably never will, If you want the stability cut the cord and go for the more structured companiesΒ 
CoorsKing
WR Officer
+13
King of the Coors Knights
Try and do both. But in the state of the market today, ESPP is not worth it IMO. I just got my recent batch and my cost basis is basically already a loss.Β 

I would go for fast moving company with 401K matching.
aiko
Politicker
+9
Sr. Account Executive
@BigMeechΒ what if its somewhere like cisco, microsoft or tesla?
CoorsKing
WR Officer
+13
King of the Coors Knights
I do work somewhere similar to that list lol. I have been here since pre-ipo when we were a true start up. My opinion is the best time to join is actually about a year POST IPO. That is when you have both name/brand recognition, as well as a good foothold in the market while at the same time you still have lots of green space to target.Β 

At that point, the stock is basically only going up, you make a lot in the role, and they still have good 401K matching.

But still, I would pick 401K over ESPP because ESPP is more volatile, and you get dinged roughly the same on taxes since you buy the stock with post-tax income and then also get taxed on the stock on both purchase and sale.
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Nairobi
Politicker
+7
BDR
I'm all about "bigger risk means bigger reward" so I'm living the startup life. But I'm sure that when I'll be older, I'll prefer an established company.
aiko
Politicker
+9
Sr. Account Executive
Love it! I felt that way with my current start up and so far were only in the negative 😩
poweredbycaffeine
WR Lieutenant
+10
Bean Juice Drinker | Sales Savant
I thrive on chaos and took this job knowing they had no corporate-sponsored retirement programs. I have my own investment strategy, and would rather get a fat base and bonus structure over other nice-to-haves.
aiko
Politicker
+9
Sr. Account Executive
Now that is something I need to look more into. Do you have a side hustle?Β 
poweredbycaffeine
WR Lieutenant
+10
Bean Juice Drinker | Sales Savant
Nopeβ€”time outside of my 8-6 is for me to do fun stuff that might kill me like skiing, mountain biking and drinking too much coffee.
TheLaughingWolf
WR Officer
+7
Account Development Representative
I'm 40 and have to take 10 different pills per day. And not the fun kind. The kind to keep you alive.

So benefits are one of the biggest deciding factors when I look for a job.Β 
Boutdamtime
Opinionated
+4
Client Executive
Holy shit you’re only 40 and on that many pills?! What?! Good luck with the next sale brotha
Sgt_Trollingham
Valued Contributor
+5
Business Development Director
I would say both are incredibly valuable, but talk to your company about what they're future plans are. If they are able to grow fast enough, eventually they will need to be competitive with benefits. If adding things like 401k matching, better healthcare, ESPP, etc. are important to you, see if they are on the roadmap. If they are, look at what that timeline looks like compared to when you would want them.Β 

I stuck it out at a start-up, 4 years in now, company is listed. I went from a junior sales rep to BDD of North America. Got stock options now, 401k matching. Improving healthcare and other benefits are my next personal missions.Β 
CharmingSalesGal
Politicker
+8
Account Executive
I'm also young-ish with no kids and recently started at a start up for the sole reason of potential to grow my career quickly. I'm ready for the next challenge and am able to individually contribute to my 401k and healthcare. My previous company had awesome benefits but sometimes I felt like I wasn't utilizing them because I'm fairly healthy and good with my money as it is.

In my ideal world, I'd have my healthcare paid for a 401k match. No need for a "cool" office with a pingpong table, LaCrap and donut Friday type shit that people deem as benefits nowadays.
rooseM3
Fire Starter
+2
Enterprise Account Executive (says)
ESPP aren't created equal. My company just went public but because of covid the commissions have dropped considerably. Feels like they are leaning heavily on the ESPP to fight the rising wave of attrition. There are a lot of things to consider when it comes to retirement planning and many ways to skin that cat!
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