Startups are messy, and exciting, and the work incentive is different. Working for a startup is awesome, and I think most people should join a startup at some point in their career. [Read also – Work in a startup 3 times in your life.]
You will be trading your time for two things – 1) accelerated learning and stacking up new skills and 2) potential financial upside in the future.
Go in with your eyes wide open and ask Questions.
If you’re thinking of joining an early stage startup, especially in a senior role, you need to ask the right questions going in.
#1 – “How many shares are outstanding and what’s the current valuation?”
This tells you what % of total shares you’ll own and how much those shares are worth, at the current valuation. Vague answers came be a flag.
#2 – “What’s a high/ medium/ low outcome for this company, and what are the likelihoods of each?”
People have different definitions of success and it’s important to know if you’re all underwriting to the same definition
#3 – “What’s the annualized value of my equity in the event of a high/med/low outcome?”
This may seem repetitive, but hearing a founder articulate this can reveal new info, and puts them in your shoes
#4 – “Would you sell, and if so when?
What does the M&A landscape look like (who, how many, how acquisitive, how deep-pocketed, and will there be bidding)?”Again, more info to help you underwrite your investment.
#5 – “How much capital is it going to take to build this company, what flavors (equity, non-dilutive), and when’s the next round?
Also, how much do the founders still own vs investors?” You’re are actually diligencing dilution + founder buy-in.
#6 -“What’s the spread between the 409a valuation and the preferred PPS at the last valuation?”
409a signals your tax obligation. PPS is closer to what the market will likely pay. Their delta tells you profit (and taxes).
#7 – “What happens if the company exits or I leave? (I don’t plan to, but tell me the rules)
“Find out if there’s an exercise window for options (you might need to save up $ like I didn’t), and if there will be accelerated vesting in an M&A or if you need to stay on at BigCo
#8 – Never be afraid to ask straight up: “As a committed early leader, I’d like to see a $[xx]M outcome from my next startup (aka, this one).
What does the roadmap look like to get there?”
#9 – Why all these questions matter:
1. As a very early senior hire, you take on (almost) all the risk of a founder but have less info on upside
2. You’re investing your life-time to make a dream come true — make sure it’s your dream, too
3. Your time > my money. You can’t go out and raise more
#10 – Final thought:
Startups are awesome, and you should definitely join one if you get a chance. [Read also – Work in a startup 3 times in your life.]