I’m getting calls from a few startups lately. I’ve never worked in a startup and feel apprehensive about it. In my early 30s and will look to start family - how bad is the work schedule and pay? Is it worth it?

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Been in startups for 5 years and have witnessed 8 total layoffs spread across each of them. I was impacted by 2 of them. Just be careful. Some red flags i’ve seen in startups that didn’t fair well:

- Company is trying to innovate too soon before finding product market fit. This may look like investing in “cool” tech that isn’t super important to the initial success of the biz
- Leadership isn’t very connected to the intended user. This will look like a lot of bad decisions in the future
- The startup is trying to structure themselves like a big company. This can mean a lot of non-essential roles and teams and too few people in the roles they actually need. These people will eventually get laid off. The people in the roles they actually need are burnt out (product + eng lol)

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Thank you!

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Only reason I’d consider startup is if I get laid off tbh

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Don’t blame you!

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You usually have a direct impact on the company. If you're the quite, hide and do your job type then it probably won't workout. They like people who are eager and have an entrepreneur mindset.

Obviously loads of risk but it can be a very rewarding job. Make sure you ask about their funding, as that's an issue with every startup.

The benefits tend to be a highly flexible lifestyle. I was able to work works wide as long as I got the target goals and kept our clients satisfied.

The downsides can be insanely unrealistic timelines, but that should come and go pretty quick. If it stays that way then you should be exiting.

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Agreed. If it’s a series C or D, definitely consider joining. I joined a pre-seed which had a toxic culture and is likely not going to secure any funding. The founders were abusive.

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Every startup is different. It boils down to leadership, profitability, product and engagement. You need to be able to really buy in so trusting that you are creating a great product matters. You want leadership to be able to act like an owner, a sales person and be great in their industry. You want the juice to be worth the squeeze, meaning if you hit your goals, there are rewards for everyone.

I've worked at 2 startups during the past 5 years. The first one became a shutdown, so not great. My current one is going well. We all see the path and are navigating it. Be prepared to do what it takes. Look to lead and pretend to be bigger than you are as a company. Find a way to keep motivating your team. If you're a product person, you probably like building things. A startup can be a great place to do that.

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I had a pretty bad experience with an early stage startup with long work hours, all weekends working, and late night calls from founders. I took up the job in August after being laid off from my last company in July. In startups (especially early stage startups), your personal life is not respected and you’re expected to be available at all times. I’ve just quit and am currently serving the notice period. I would suggest taking up the role and continuing to explore better opportunities.

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I've been in demanding and not-too-demanging startups (many years ago).
I'd echo other comments about checking the founders and culture before joining - look for people who have worked with them before and avoid toxic ones.
Good comment below about ensuring they relate to the real customers.

Another aspect of success is thinking about distribution equally with product-market fit.

A great product that nobody can discover won't generate growth and will lead to early death or endless pivots and misery.
The truism is that the 2nd startup of every founder focuses on distribution over product because it's so essential for growth and scaling. So check that during interviews and even about prior startups by the same founders and team.

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Startups can be fun. It's crazy, hectic, lots of work, and your role may change regularly. You'll wear multiple hats and learn a LOT about everything.

Startups have terrible benefits. If you have serious or chronic medical conditions (or your dependents do) then a startup may not be a great fit.

If you're trying to get pregnant or need IVF to get pregnant, then those startup medical benefits probably won't help much. And the work-life balance may make it more difficult.

However, if you're flexible, and especially if you're married or in a relationship with someone else who has a good job, then definitely try a startup. You can learn more, make more connections, get early stage equity, and get the scars necessary to make you a kickass employee or become your own boss later.

I'm in my early 50s. I've worked for 4 startups. 3 of those gave me equity. 2 of those 3 were eventually sold and I made a nice profit (small house money and new car money). The 3rd one is still pending and it'll be another few years before I find out how that goes.

I would work for another startup now, but I admit that the older I get the harder it is to bring the energy to bear that a startup needs. So do it while you're young and you can. Those boring stable jobs will always be there waiting if you don't like it.

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Consider how much stability you need. 1 year too short? How about 2-3 years? Sound good? Work that into your explorative conversations.

What can you gain with each opportunity?

Flat organization with a ton of autonomy? A great mentor who has launched some cool products from 0-1?

Since you mention you’re about to start a family ask about their benefits.

Learning curve is high but so much work and pressure. You learn a lot and wear multiple hats and you might not build a vertical experience or focus on one Expertise.
My advice is to check if the company have diverse roles, this way you will know that the hats you will wear is minimal and you will focus on your specialty. Good luck. Also insist on getting stock options

I worked at a startup for 3 1/2 years. Very little layoffs happened during that time. It was so much fun, but also a lot of work as I wore many hats.

Before thinking about it, make sure you know how well funded they are. You can research online but ask as well. It is important to know what you are getting into. Also, be wary of options instead of part of your salary. if they offer you that, don't walk away - run!

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