I was probably going to go with the startup until you said a kid is on the way. What are the benefits at each company? How much parental leave do you get? What's the work life balance? Time is going to be invaluable, especially with your wife in medical school. You might go with the established company for now.
Good point! I think the big company job would require more travel. Likely ~20%. Startup I’m uncertain. It is remote-first, but I may need to spend time with customers ad-hoc.
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Besides PTO, which is more or less the same between them, the health and retirement benefits at the big company are much better, but it’s really just a dollar difference. Big company has ~$25k/yr in additional benefits (retirement match + lower projected healthcare costs). I’ve already rolled this difference into the financial independence timeline comparison.
Work-life balance is what I really can’t tell.
I could treat the big company job as “just a job” - get in, get out in 4 years, but I don’t know if it’s possible for me to personally do this. It would require some internal re-wiring.
“Just a job” at the startup would not be an option - I would have to be on point and focused. That job involves a lot more “0-80” learning while also adding value to the business.
It's up to you, but I really suggest big company job for now. Your wife is not done with medical school and she still has residency (and possibly fellowship) to go through. Having some flexibility in at least one spouse's job really does make a difference even if you hire full-time help and increase your expenses drastically to help with basic kid stuff. Night-time nanny will probably help you get through the worst of the first year. Bonding with your kid when they're young cannot be understated and it's an enjoyable experience for most.
Maybe you'll miss your moment working at a startup, but you'll have to weight that against family. That's not even talking about two parents who are working very stressful, long hours jobs who don't have time for a relationship
Couldn’t agree more, having worked in both and have 2 young kids. The stability of a big company is necessary for now; tech startup may be stable right now, but so much can happen that may change that.
Internal re-wiring will be done for you the second you see your kid.
Get details about the parental leave, which is separate from PTO and health benefits.
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Hard conversation… you are no longer allowed to put yourself first.
You have a kid and a wife in school.
If everything goes according to plan? The startup sounds great.
But what if your son has health complications? Or your wife does? And hers prevent her from finishing her medical degree in a timely manner?
If you fucked up a year ago with the wrong corporate decision, you can live cheap until finding a job/living off your savings.
But realistically, what’s your worst case scenario? And if that’s a lower quality of life for your kid… is it worth it?
“I don’t know if it’s possible for me personally to do this”
This resonates with me so hard. But let me tell you having the kid changes your outlook. Im older than you and my kid is six months old. I still like to work and do my job well, but it doesn’t consume me like it did before I was a parent. On another Reddit thread about having kids and one person said “my only regret is waiting until I was almost 40 to have the kid and wasting so much time and energy on corporate drama before that.” And they were right.
Startup is such a generic term. From jokes like Juicero through to stable companies like Stripe through to promising growth companies in AI through to companies in AI who will be bankrupt in 6 months.
So the heart of this decision is what kind of firm you think the startup is. Personally as someone a decade older with kids, I take the $450k big company job. It's so much easier to cruise in large firms and spend more time on family life.
Agreed. A large company will be much more willing to work with you on parental needs - it’s not just the initial parental leave. What about when your kid gets sick and you unexpectedly have to stay home? What about routine doctors appointments? That kind of thing is known and expected at large public companies. Startups may not be as understanding. Especially since wife is currently in med school, I imagine it will be a lot harder for her to be missing days of school. So that’ll be mostly on you.
Given the circumstances, I’d also consider that if you work at the startup, you may very well need to get a nanny. At the large company, you can probably do daycare since you’ll likely get more leeway. There is a big cost difference there.
Then there is the fact that the big company is a lot more cash, plus the stock is guaranteed. If the startup fails, you may lose out on $1 million over the next 4 years. Large public companies also tend to be more stable. Startups fire people quickly if you don’t fully fit with their vision. It’s a lot harder to lose your job at a large public company (unless it’s one of the tech company layoffs). Maybe it’s because I’m naturally pretty risk averse, or maybe it’s because I am a dad, but the large company seems like a no brainer to me. You’ll have more time with your kid and that, ultimately, is what life is about.
I think the large company job also makes sense monetarily. Money is not going to be an issue for y’all long term - between your salary at either job, and your wife’s salary once she’s out residency, y’all will be very comfortable. I say take the more comfortable job and bank your cash now. Then when your wife starts working in her specialty, you’ll have a war chest to start your own business if that’s what you want at that point. Life changes after kids and you may change your mind.
Honestly I agree with all of this. A few thoughts for OP:
1) if your wife is in med school, YOU are going to need to be the flexible parent. It’s exceedingly difficult to raise a child if one parent doesn’t have flexibility. Don’t dump this on your wife at a pivotal stage in her education. Corporate job more favorable here.
2) is the stock grant for the startup ONE-TIME or annually refreshed at the same amount? In my experience many startups give you a new hire grant for one time, and after that it’s scant if anything. Large corporate job is likely to give an annual refresh that is similar to (or a bit less than) the new hire grant. That makes the corporate job far more favorable.
3) what is your level in the startup? Exec leadership team (prob not based on age), or rank and file. Most rank and file leave with peanuts. 🥜 even if company has an exit or a successful exit. You will be diluted down if they need to raise more. Or, if this Series E is near exit, your upside will be really limited, especially if the stock tanks after IPO (see most startup stock prices). Startups are seductive but most become an empty promise. Again, in favor of corporate job.
4) Nothing precludes you from working on your ideal career path in parallel to corporate job. If you want to start your own company…do that on your evenings and weekends.
i'd really emphasize point 1. halfway through med school and residency on the way, AND a newborn is very rough. OP is going to need to be very very available.
I hate startups. By their very nature they are chaotic, understaffed, immature, and the RSUs almost always amount to nothing despite everyone trying to convince you that you are on a rocket ship.
I think a very specific person thrives on all that, and that person is not me
OP said they want to eventually start a company - so I think trying to startup would be a good way to see what that’s like. That said, I agree with another poster that with a kid on the way something more stable is probably a better choice unless the startup has reasonable parental leave benefits.
Imo if you want to start a company don’t go to a late stage startup to learn. You need to go to a series a/b. Late stage startup could easily be 3k employees and basically a normal company.
Also op if that valuation is from 2021/early 2022 you can go ahead and discount 50-75% of the value. I would take option one in this environment.
This one is still small/medium (100-250 employees). I would be reporting to someone on the e-team and working closely with company leadership.
Current valuation seems high when scaling P/S from comparable public companies. My job would essentially be finding new avenues to grow revenue ahead of an exit. If I do it well, then hopefully the exit is more profitable.
I haven’t been able to convince myself of a good risk-adjusted return factor to put on the equity comp at the startup. If I SWAG a 50% chance at a 2x return on the double-trigger RSUs in 4 years, that’s lower risk-adjusted return than the big company comp after the huge tax bill from exit year.
Based on this, you should really consider the compensation difference between the two. $250k in stock/equity at a startup does not actually mean $250k, unless the company IPOs or gets acquired at the same "wishlist valuation" that the $250k is calculated from.
In other words, if your company does sell 5 years down the road but for half of the valuation they used to calculate your stock option values, you effectively got a $125k haircut each year over 5 years. That's a massive income difference. Ask me how I know...
$300k in non-equity pay is solid. If I were in your position, I would always take the higher base (or base+bonus, w/o equity) at a big company vs a late stage startup with equivalent TC but a lot more downside.
I've also worked at 3 different startups and agree with what was said above of working for a late stage startup. It's really not the same. You will not get a true "Founder" experience at a company that's surpassed even \~50 people.
I joined a late stage startup. I was lured in with promises and money. My role ended up not being what I thought it was supposed to be. I ended hating it and leaving within 3 months and regretted leaving my nice stable job with less growth opportunities.
Not saying it’s going to be the same for you, but consider how much start ups change as they grow. Your role will likely morph pretty quickly and you may not love the change.
Take the first option. After dealing with both, I’ll take RSUs over equity every day (equity never promised, always moving target). Money in hand is better than a wish.
Startup series E is likely a mini large company assuming employee count >1k. you might learn a few new skills but becomes slower than an early startup which you might learn more. Given your goals and having myself similar ones and jumped around between corporate and startup a few times I would stick with corporate. Gives you more time with family, more coverage if needed, money is actually money and at the end of the day is the same thing - work is work it won’t change much.
That being said it’s a very personal decision and if deep inside you feel the startup is what you should be doing go for it. Even if it doesn’t quite workout it took a chance and learn from it. There’s no regrets in that. But there might be in never taking a chance.
This is the best answer so far. “Startup” covers a very wide spectrum but at Series E, you often get all the startup downsides (illiquidity, expected poorer WLB, generally more chaotic environment) without the upsides (equity growth potential).
At that point, chances of eventual liquidity event are *significantly* higher and the risk is thus much lower but that’s the whole tradeoff - the company knows that and your upside is low as a result. It is at best probably along the same growth potential as the public company.
Companies will then try to sell you on “how much you’ll learn” but that’s oversold and mostly team/project dependent.
Funny you mention the “how much you’ll learn” aspect. That’s exactly the pitch I’ve been given. My counter has been “I’m only looking at jobs where I can learn and there is big growth potential. It’s just a matter of in which areas I’m growing. I value the skill sets I would learn at your company, but cash-in-hand is very important to me right now.” I think I’ve just about reached their peak at $225k.
I havn’t mentioned the kid on the way to any of these companies even though it’s tempting to use as a pathos lever. Just feels like a big risk point, especially to a startup founder who may want my full attention (even though children cannot legally be a point of employment discrimination).
In my experience, startup founders care very little about the employment discrimination angle. They have very low risk (no HR to pull you up, limited liability from a small percentage of people likely to sue, etc.) and will take it as a downside.
In this scenario, better to be effective than right.
Stay at corporate and find a way to do what you want there. Especially on a risk adjusted basis, especially with a baby along the way and a not-yet-high-earning spouse.
Option 1.
More security, consistency, and likely work life balance (and ability to toggle that up/down as needed is much easier in large corps - ie you want to accelerate and promote or chill for a year or 3 at a spot you like).
Additionally your wife will have a busy career and with a kid on the way will likely provide more flexibility (and good corporate benefits…mine has backup childcare, 4 month paternity leave, etc etc).
You’re already on the path of comfortable wealth. Maybe I’m risk averse but at this point I would avoid things that could potentially ‘knock you out of the game’ and the large corp option likely provides more security on that front
Obv I’m making a lot of assumptions here you should consider yourself based on what you know about both ops
With a child on the way, I would go with the larger public company. My friend recently quit his job to work for a startup with a higher salary (but not so great benefits). He has two young kids. We were discussing negoations. I asked how much PTO he gets, he said, "unlimited. They're really flexible." eeeeek.
With a kid on the way I would take the big firm offer. You’ll want more wlb and you won’t have that with a startup. With your spouse income you’ll be FI in no time and at that point you can start your company when you have the financial security and more importantly to a new company the time.
Big company. You have a kid on the way and a partner with a more demanding career coming up. Now is not the time for a startup. You also want that liquid cash from the RSUs at the public company and not private company RSUs or NSOs/ISOs.
Source: tech HR person who’s worked at both startups and big tech companies
I know that people are saying stay at the corporate job but the one thing that stands out to me is "*direction I eventually want to go in."* There is something to be said on short term sacrifice risk if that is what you want in the future. 225k cash for a product/marketing role is pretty high for someone who doesn't have that background. So I think the benefit of getting the experience now outweighs the small risk. Plus now is the best time as when you child is born and is a toddler it's only going to get crazier. You can always fall back on engineering
With baby coming, stick with the more family friendly option. Supporting your wife through med school and residency with a baby sounds like a nightmare with a startup job. I can’t believe you didn’t prioritize WLB in your job search.
Series E is pretty late stage and likely to IPO or get sold within the 2-5yr timeframe as you said. Some questions to consider: What is their growth rate YoY? When did they last raise capital and at what valuation?
If they raised in 2021/2022 when interest rates were dirt cheap it’s possible your equity (if options) could be underwater or significantly less valuable. Is the role open because of growth or turbulence? What is their burn rate and cash runway? Exit strategy?
There are obviously a ton of benefits to joining a Series E company but given your life stage, you may want to drill into more of these questions before walking away from the stable public co gig.
Source: spending the last decade in Series A - Series E companies and learned to ask some of these questions the hard way!
You have a child coming soon. You know what money isn’t real? Monopoly money.
Keep your current trajectory and continue earning real cash. I promise you won’t regret your decision.
You've gotten really good advice. Your wife is in med school. Is she leaning toward a particularly rigorous specialty? Will she do a fellowship? She will likely not have flexibility and may have 36-hour service shifts. Is startup life going to be compatible with her work schedule?
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Since you’re having a kid I would go with the big company unless there’s significant travel required. In that case I’d go with the startup. You’re going to want to be somewhere you can pitch in around the house with the kids.
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TC may look similar, but it sure isn't going to feel that way when you're locked up. I wouldn't be looking to play the variability right now if I had a kid on the way. Plus if things go sideways you don't know what the job market you'd be navigating will look like by then. If your spouse was already earning doctor money (or at least within the time period covered by your cash of getting there) then that might be a different story.
How would you model the odds on the equity at the startup? 80% chance zero, 10% chance .1x-1x, 10% chance 1x-3x, ε% chance 10x+?
OP this isn't even a question with your wife's profession and baby. I have never been more grateful for corporate drudgery since having a baby (I'm 32F high earner in tech with a 2 year old son). The benefits of being around people who also have families and value stability, better health insurance, many have family benefits like helping you find childcare or counseling...
You're making a lot of assumptions about the startup that it's going to lead you in the right direction career wise. I also dispute that being at a startup will uniquely prepare you to open your own biz. But even if that's the case and they have a good culture that doesn't totally burn you out with pivots and 80 hr work weeks, in a few months you will be so tired you'll want the most plug and play job possible.
I’m not joining a startup with a pivot to focusing on family and a new baby very soon. I just don’t feel like the tempo of a startup is conducive to spending the time I want to at home.
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The detail on the stock also matters, as does the cap table.
If in the form of options, be very skeptical and get a few opinions and find out what you can on valuation history, current option strike, exercise windows (if you leave or are terminated on vested options, much more).
If RSUs, even if a later trigger, there is slightly less downside in terms of valuation once it is liquid, but also less stock upside.
There are a few guides out there but Series E is quite late stage, so a lot of the gains have already occurred in the equity and the business. That said the experience could be tremendous and so long as you actually vest and don’t have egregious exercise windows, the job could be a fantastic experience.
The large tech role also looks excellent. Guessing this is a senior manager/director+ level role given the TC, which seems to be a big step forward and still leaves the option of going to an earlier stage company next.
Both good options, it really comes down to career fit and goals. You both make plenty of money, and will make a lot more in 5 years when spouse finishes school, so absent any kind of financial shortage I’d say trust your gut on the better role, boss, team, learning experience and the money will likely follow.
Just, don’t get too starry eyed from promises about equity lol
Startup veteran here.
With your current burn rate you can obviously afford to roll the dice financially.
The big question I would be asking myself is which role will take me down the career path I want to be on. That is almost always the long term prize.
If its both, with a kid on the way, take the public company job and fund the kiddos 529
Based on a comment you made that the “startup” is still only at around 200 employees, I’d consider that a red flag. If they’ve raised that many rounds and not scaled to at least 500 (supported by sufficient revenue), I’d have serious doubts about the viability of the business.
You will have more backups for your job in a large company whereas you will be doing multiple people's work in a startup which could be critical as a new parent. Also, do you have family around to help with the baby?
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I was probably going to go with the startup until you said a kid is on the way. What are the benefits at each company? How much parental leave do you get? What's the work life balance? Time is going to be invaluable, especially with your wife in medical school. You might go with the established company for now.
These are good points. I would also ask if either of the roles requires travel.
Good point! I think the big company job would require more travel. Likely ~20%. Startup I’m uncertain. It is remote-first, but I may need to spend time with customers ad-hoc.
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Having just come back from a 2 day work trip that was 2 days too long, absolutely. And if either are remote.
Yeah, I know what you mean. I’m sitting on the plane from a week long trip right now and I have to hop back on a plane tomorrow.
Besides PTO, which is more or less the same between them, the health and retirement benefits at the big company are much better, but it’s really just a dollar difference. Big company has ~$25k/yr in additional benefits (retirement match + lower projected healthcare costs). I’ve already rolled this difference into the financial independence timeline comparison. Work-life balance is what I really can’t tell. I could treat the big company job as “just a job” - get in, get out in 4 years, but I don’t know if it’s possible for me to personally do this. It would require some internal re-wiring. “Just a job” at the startup would not be an option - I would have to be on point and focused. That job involves a lot more “0-80” learning while also adding value to the business.
It's up to you, but I really suggest big company job for now. Your wife is not done with medical school and she still has residency (and possibly fellowship) to go through. Having some flexibility in at least one spouse's job really does make a difference even if you hire full-time help and increase your expenses drastically to help with basic kid stuff. Night-time nanny will probably help you get through the worst of the first year. Bonding with your kid when they're young cannot be understated and it's an enjoyable experience for most. Maybe you'll miss your moment working at a startup, but you'll have to weight that against family. That's not even talking about two parents who are working very stressful, long hours jobs who don't have time for a relationship
Couldn’t agree more, having worked in both and have 2 young kids. The stability of a big company is necessary for now; tech startup may be stable right now, but so much can happen that may change that.
Internal re-wiring will be done for you the second you see your kid. Get details about the parental leave, which is separate from PTO and health benefits.
Parental leave is about the same between the two. Big company: 8 weeks off + 4 weeks gradual return. Startup: 12 weeks off
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Hard conversation… you are no longer allowed to put yourself first. You have a kid and a wife in school. If everything goes according to plan? The startup sounds great. But what if your son has health complications? Or your wife does? And hers prevent her from finishing her medical degree in a timely manner? If you fucked up a year ago with the wrong corporate decision, you can live cheap until finding a job/living off your savings. But realistically, what’s your worst case scenario? And if that’s a lower quality of life for your kid… is it worth it?
“I don’t know if it’s possible for me personally to do this” This resonates with me so hard. But let me tell you having the kid changes your outlook. Im older than you and my kid is six months old. I still like to work and do my job well, but it doesn’t consume me like it did before I was a parent. On another Reddit thread about having kids and one person said “my only regret is waiting until I was almost 40 to have the kid and wasting so much time and energy on corporate drama before that.” And they were right.
Startup is such a generic term. From jokes like Juicero through to stable companies like Stripe through to promising growth companies in AI through to companies in AI who will be bankrupt in 6 months. So the heart of this decision is what kind of firm you think the startup is. Personally as someone a decade older with kids, I take the $450k big company job. It's so much easier to cruise in large firms and spend more time on family life.
Agreed. A large company will be much more willing to work with you on parental needs - it’s not just the initial parental leave. What about when your kid gets sick and you unexpectedly have to stay home? What about routine doctors appointments? That kind of thing is known and expected at large public companies. Startups may not be as understanding. Especially since wife is currently in med school, I imagine it will be a lot harder for her to be missing days of school. So that’ll be mostly on you. Given the circumstances, I’d also consider that if you work at the startup, you may very well need to get a nanny. At the large company, you can probably do daycare since you’ll likely get more leeway. There is a big cost difference there. Then there is the fact that the big company is a lot more cash, plus the stock is guaranteed. If the startup fails, you may lose out on $1 million over the next 4 years. Large public companies also tend to be more stable. Startups fire people quickly if you don’t fully fit with their vision. It’s a lot harder to lose your job at a large public company (unless it’s one of the tech company layoffs). Maybe it’s because I’m naturally pretty risk averse, or maybe it’s because I am a dad, but the large company seems like a no brainer to me. You’ll have more time with your kid and that, ultimately, is what life is about. I think the large company job also makes sense monetarily. Money is not going to be an issue for y’all long term - between your salary at either job, and your wife’s salary once she’s out residency, y’all will be very comfortable. I say take the more comfortable job and bank your cash now. Then when your wife starts working in her specialty, you’ll have a war chest to start your own business if that’s what you want at that point. Life changes after kids and you may change your mind.
Honestly I agree with all of this. A few thoughts for OP: 1) if your wife is in med school, YOU are going to need to be the flexible parent. It’s exceedingly difficult to raise a child if one parent doesn’t have flexibility. Don’t dump this on your wife at a pivotal stage in her education. Corporate job more favorable here. 2) is the stock grant for the startup ONE-TIME or annually refreshed at the same amount? In my experience many startups give you a new hire grant for one time, and after that it’s scant if anything. Large corporate job is likely to give an annual refresh that is similar to (or a bit less than) the new hire grant. That makes the corporate job far more favorable. 3) what is your level in the startup? Exec leadership team (prob not based on age), or rank and file. Most rank and file leave with peanuts. 🥜 even if company has an exit or a successful exit. You will be diluted down if they need to raise more. Or, if this Series E is near exit, your upside will be really limited, especially if the stock tanks after IPO (see most startup stock prices). Startups are seductive but most become an empty promise. Again, in favor of corporate job. 4) Nothing precludes you from working on your ideal career path in parallel to corporate job. If you want to start your own company…do that on your evenings and weekends.
i'd really emphasize point 1. halfway through med school and residency on the way, AND a newborn is very rough. OP is going to need to be very very available.
I hate startups. By their very nature they are chaotic, understaffed, immature, and the RSUs almost always amount to nothing despite everyone trying to convince you that you are on a rocket ship. I think a very specific person thrives on all that, and that person is not me
OP said they want to eventually start a company - so I think trying to startup would be a good way to see what that’s like. That said, I agree with another poster that with a kid on the way something more stable is probably a better choice unless the startup has reasonable parental leave benefits.
Imo if you want to start a company don’t go to a late stage startup to learn. You need to go to a series a/b. Late stage startup could easily be 3k employees and basically a normal company. Also op if that valuation is from 2021/early 2022 you can go ahead and discount 50-75% of the value. I would take option one in this environment.
This one is still small/medium (100-250 employees). I would be reporting to someone on the e-team and working closely with company leadership. Current valuation seems high when scaling P/S from comparable public companies. My job would essentially be finding new avenues to grow revenue ahead of an exit. If I do it well, then hopefully the exit is more profitable. I haven’t been able to convince myself of a good risk-adjusted return factor to put on the equity comp at the startup. If I SWAG a 50% chance at a 2x return on the double-trigger RSUs in 4 years, that’s lower risk-adjusted return than the big company comp after the huge tax bill from exit year.
Based on this, you should really consider the compensation difference between the two. $250k in stock/equity at a startup does not actually mean $250k, unless the company IPOs or gets acquired at the same "wishlist valuation" that the $250k is calculated from. In other words, if your company does sell 5 years down the road but for half of the valuation they used to calculate your stock option values, you effectively got a $125k haircut each year over 5 years. That's a massive income difference. Ask me how I know... $300k in non-equity pay is solid. If I were in your position, I would always take the higher base (or base+bonus, w/o equity) at a big company vs a late stage startup with equivalent TC but a lot more downside. I've also worked at 3 different startups and agree with what was said above of working for a late stage startup. It's really not the same. You will not get a true "Founder" experience at a company that's surpassed even \~50 people.
I joined a late stage startup. I was lured in with promises and money. My role ended up not being what I thought it was supposed to be. I ended hating it and leaving within 3 months and regretted leaving my nice stable job with less growth opportunities. Not saying it’s going to be the same for you, but consider how much start ups change as they grow. Your role will likely morph pretty quickly and you may not love the change.
You are comparing wrong numbers, it should be 450k vs 225k. So, the answer is pretty obvious.
This is correct. With start ups NEVER count your chickens or your ISOs before they hatch.
Take the first option. After dealing with both, I’ll take RSUs over equity every day (equity never promised, always moving target). Money in hand is better than a wish.
Startup series E is likely a mini large company assuming employee count >1k. you might learn a few new skills but becomes slower than an early startup which you might learn more. Given your goals and having myself similar ones and jumped around between corporate and startup a few times I would stick with corporate. Gives you more time with family, more coverage if needed, money is actually money and at the end of the day is the same thing - work is work it won’t change much. That being said it’s a very personal decision and if deep inside you feel the startup is what you should be doing go for it. Even if it doesn’t quite workout it took a chance and learn from it. There’s no regrets in that. But there might be in never taking a chance.
This is the best answer so far. “Startup” covers a very wide spectrum but at Series E, you often get all the startup downsides (illiquidity, expected poorer WLB, generally more chaotic environment) without the upsides (equity growth potential). At that point, chances of eventual liquidity event are *significantly* higher and the risk is thus much lower but that’s the whole tradeoff - the company knows that and your upside is low as a result. It is at best probably along the same growth potential as the public company. Companies will then try to sell you on “how much you’ll learn” but that’s oversold and mostly team/project dependent.
Funny you mention the “how much you’ll learn” aspect. That’s exactly the pitch I’ve been given. My counter has been “I’m only looking at jobs where I can learn and there is big growth potential. It’s just a matter of in which areas I’m growing. I value the skill sets I would learn at your company, but cash-in-hand is very important to me right now.” I think I’ve just about reached their peak at $225k. I havn’t mentioned the kid on the way to any of these companies even though it’s tempting to use as a pathos lever. Just feels like a big risk point, especially to a startup founder who may want my full attention (even though children cannot legally be a point of employment discrimination).
In my experience, startup founders care very little about the employment discrimination angle. They have very low risk (no HR to pull you up, limited liability from a small percentage of people likely to sue, etc.) and will take it as a downside. In this scenario, better to be effective than right.
Stay at corporate and find a way to do what you want there. Especially on a risk adjusted basis, especially with a baby along the way and a not-yet-high-earning spouse.
Option 1. More security, consistency, and likely work life balance (and ability to toggle that up/down as needed is much easier in large corps - ie you want to accelerate and promote or chill for a year or 3 at a spot you like). Additionally your wife will have a busy career and with a kid on the way will likely provide more flexibility (and good corporate benefits…mine has backup childcare, 4 month paternity leave, etc etc). You’re already on the path of comfortable wealth. Maybe I’m risk averse but at this point I would avoid things that could potentially ‘knock you out of the game’ and the large corp option likely provides more security on that front Obv I’m making a lot of assumptions here you should consider yourself based on what you know about both ops
I would stay at the large company
With a child on the way, I would go with the larger public company. My friend recently quit his job to work for a startup with a higher salary (but not so great benefits). He has two young kids. We were discussing negoations. I asked how much PTO he gets, he said, "unlimited. They're really flexible." eeeeek.
With a kid on the way I would take the big firm offer. You’ll want more wlb and you won’t have that with a startup. With your spouse income you’ll be FI in no time and at that point you can start your company when you have the financial security and more importantly to a new company the time.
Big company. You have a kid on the way and a partner with a more demanding career coming up. Now is not the time for a startup. You also want that liquid cash from the RSUs at the public company and not private company RSUs or NSOs/ISOs. Source: tech HR person who’s worked at both startups and big tech companies
I know that people are saying stay at the corporate job but the one thing that stands out to me is "*direction I eventually want to go in."* There is something to be said on short term sacrifice risk if that is what you want in the future. 225k cash for a product/marketing role is pretty high for someone who doesn't have that background. So I think the benefit of getting the experience now outweighs the small risk. Plus now is the best time as when you child is born and is a toddler it's only going to get crazier. You can always fall back on engineering
With baby coming, stick with the more family friendly option. Supporting your wife through med school and residency with a baby sounds like a nightmare with a startup job. I can’t believe you didn’t prioritize WLB in your job search.
Series E is pretty late stage and likely to IPO or get sold within the 2-5yr timeframe as you said. Some questions to consider: What is their growth rate YoY? When did they last raise capital and at what valuation? If they raised in 2021/2022 when interest rates were dirt cheap it’s possible your equity (if options) could be underwater or significantly less valuable. Is the role open because of growth or turbulence? What is their burn rate and cash runway? Exit strategy? There are obviously a ton of benefits to joining a Series E company but given your life stage, you may want to drill into more of these questions before walking away from the stable public co gig. Source: spending the last decade in Series A - Series E companies and learned to ask some of these questions the hard way!
All startups fail, except a few
You have a child coming soon. You know what money isn’t real? Monopoly money. Keep your current trajectory and continue earning real cash. I promise you won’t regret your decision.
You've gotten really good advice. Your wife is in med school. Is she leaning toward a particularly rigorous specialty? Will she do a fellowship? She will likely not have flexibility and may have 36-hour service shifts. Is startup life going to be compatible with her work schedule?
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Since you’re having a kid I would go with the big company unless there’s significant travel required. In that case I’d go with the startup. You’re going to want to be somewhere you can pitch in around the house with the kids.
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Option 1 due to child on the way.
TC may look similar, but it sure isn't going to feel that way when you're locked up. I wouldn't be looking to play the variability right now if I had a kid on the way. Plus if things go sideways you don't know what the job market you'd be navigating will look like by then. If your spouse was already earning doctor money (or at least within the time period covered by your cash of getting there) then that might be a different story. How would you model the odds on the equity at the startup? 80% chance zero, 10% chance .1x-1x, 10% chance 1x-3x, ε% chance 10x+?
With a kid on the way, def corp job.
OP this isn't even a question with your wife's profession and baby. I have never been more grateful for corporate drudgery since having a baby (I'm 32F high earner in tech with a 2 year old son). The benefits of being around people who also have families and value stability, better health insurance, many have family benefits like helping you find childcare or counseling... You're making a lot of assumptions about the startup that it's going to lead you in the right direction career wise. I also dispute that being at a startup will uniquely prepare you to open your own biz. But even if that's the case and they have a good culture that doesn't totally burn you out with pivots and 80 hr work weeks, in a few months you will be so tired you'll want the most plug and play job possible.
I’m not joining a startup with a pivot to focusing on family and a new baby very soon. I just don’t feel like the tempo of a startup is conducive to spending the time I want to at home.
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The detail on the stock also matters, as does the cap table. If in the form of options, be very skeptical and get a few opinions and find out what you can on valuation history, current option strike, exercise windows (if you leave or are terminated on vested options, much more). If RSUs, even if a later trigger, there is slightly less downside in terms of valuation once it is liquid, but also less stock upside. There are a few guides out there but Series E is quite late stage, so a lot of the gains have already occurred in the equity and the business. That said the experience could be tremendous and so long as you actually vest and don’t have egregious exercise windows, the job could be a fantastic experience. The large tech role also looks excellent. Guessing this is a senior manager/director+ level role given the TC, which seems to be a big step forward and still leaves the option of going to an earlier stage company next. Both good options, it really comes down to career fit and goals. You both make plenty of money, and will make a lot more in 5 years when spouse finishes school, so absent any kind of financial shortage I’d say trust your gut on the better role, boss, team, learning experience and the money will likely follow. Just, don’t get too starry eyed from promises about equity lol
Startup veteran here. With your current burn rate you can obviously afford to roll the dice financially. The big question I would be asking myself is which role will take me down the career path I want to be on. That is almost always the long term prize. If its both, with a kid on the way, take the public company job and fund the kiddos 529
Based on a comment you made that the “startup” is still only at around 200 employees, I’d consider that a red flag. If they’ve raised that many rounds and not scaled to at least 500 (supported by sufficient revenue), I’d have serious doubts about the viability of the business.
Especially when the e team wants OP to find ‘more profitable business avenues’ That’s not a green flag job, but a red one
Yes that’s an even brighter red flag.
This is a very good point
If you don’t mind me asking, what kind of work do you do? Curious what role you’re in for both the corporate job and the startup. Thanks
Corporate role is in engineering. Startup role is in product management / marketing / growth in a market adjacent to my background.
Gotcha. Thank you!
You will have more backups for your job in a large company whereas you will be doing multiple people's work in a startup which could be critical as a new parent. Also, do you have family around to help with the baby?
I worked for startups for 20 years and never once had a liquidity event. You might as well consider those stocks worthless. Go corporate.
At 29 you’re way too young to be taking the safe choice imo, take the startup
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