I put up the following response and have turned it into a short blog post which I hope will be helpful for anyone exploring a gig in the startup sector. Would also appreciate hearing your insights and reflections.
Thanks for the great post and doing so much to help job seekers in these challenging times. This really shows the power and impact of LinkedIn.
Having founded a small startup PCDN.Global (after being a professor for 10 years at Georgetown University) I can say it is an amazing journey. But obviously it can be very challenging compared to having a job with stable salary, benefits and more. A few things I would suggest to people looking to work for a startup whether during challenging or good economic times are outlined below:
1) Very few organizations these days guarantee long-term jobs - For most job holders, job certainty is becoming a relic of the past. Whether one works for a large corporation, university, nonprofit, in most sectors these days there is always the danger of losing one's job due to economic or organizational changes. In addition, I remember years ago it was frowned about to switch jobs too often. Now in many sectors it is becoming increasingly common to switch positions every few years. Employees are also using their own agency to leave positions when they may have previously stayed at for a long period.
2) Startups are Amazing & Exhausting - If you want to work for a startup in most cases be prepared to work hard. It can be very exciting to help build a new company, product or service, but be aware this can require working far beyond the normal 35-40 hours (although some startups do put a strong emphasis on work/life balance). While exponential growth (including in one's career and salary) can happen, many startups fail and there can be an incredible amount of stress in the process. Look beyond the hype of startups are cool to also understand the day to day reality.
3) Interview the Startup as they interview you - There are many startups with great work cultures, but as we all know there are also ones that have very unhealthy cultures. Do your due diligence about places you might be seeking to work at or interviewing for before saying yes to an opportunity. Explore how they treat employees, what are their core values, what is your potential manager like, what does the CEO or leadership team communicate publicly. Ask your peers, use networks such as Linkedin and Glassdoor (with a grain of salt). Ask or explore questions such as
4) Look at the metrics - When starting a job it is appropriate to get know how much capital does the company have to grow. Do they have a runway of 2 months or 24 months? When was their last capital raise? When will there next one be? Using platforms such as AngelList & Crunchbase among others can also provide valuable insights.
5) Look at your financials - Working for a startup can be risky (but also rewarding professionally and financially). Examine if you have enough money saved up (an emergency fund) in case the startup fails? If you will receive equity explore how long it takes to vest? Can you do a small side gig to help supplement your income?
6) Are you excited to learn and build? One of the things I love about startups is the rapid learning, iterating, and constant need to explore new areas. Are you excited about this fun but very uncertain journey or do you need or want more stability?
7) Develop Your Own Career Path - You need to be your own advocate and consider how this potential job will help you advance your skills, experience and career path.
I have friend's who have taken positions at "stable" organizations to get laid off within a few months due to financial challenges. While this is more likely to happen at a startup, if you come with a growth mindset, are aware of the realistic opportunities and challenges, and run the numbers working at a startup can be a great choice.