Community Discussion: An old colleague reached out to ask if I'm interested in joining his startup as their only lawyer. What should I consider or ask my colleague?

In-house Counsel talk through what counsel would need to know before becoming the only lawyer at a company.

(Author) Commercial Counsel:
An old business colleague reached out to ask if I had any interest in joining their startup as their only lawyer. It wouldn’t be a GC role and would be focused on sales deals and vendor contracts. I am comfortable with both, but sales is more in my wheelhouse. The role sounds interesting, but I have never been the sole in-house lawyer and the thought is a bit daunting. It sounds like there would be budget to engage outside counsel as needed. What else should I consider or ask my colleague?

In-House Counsel Responses:

Not sure of your current role or the limitations of your current role - but could they bring you on as a part-time outside GC? And if it all goes well, bring you in FT if you like. (I knew a GC for a fiber company that did this, and it worked out great). - Just trying to figure out a way to minimize your potential risks.
- Thanks, it sounds like there would be enough deal work for this to be FT. My current role is comfortable and not super exciting, but otherwise I don’t really have any complaints (I've only been here for less than 7 months, though). I wouldn’t mind a bit more of a fast-paced work environment, but I also enjoy not working on weekends and not having long hours everyday.
  - That makes sense. Be careful what you ask for though. Many attorneys are trying to get where you are and it may not be easy for you to transition back to a slower pace. I think it depends on your priorities (immediate and near future).
For me, I have a young family, so WLB and slower pace is GOLD. I would happily take a pay cut for it. My three-year-old asked - "what are you doing here?", I was confused and my spouse explained that my kid thought I lived somewhere else (because I'm always at work). FML. Knowing what I know now, I would have started the process of a slower practice three years ago. - Sorry, I digressed. - If I was in your position, I would want to know the company's financials and stability. Having work does not mean they are stable. Any regulatory issues that are specific to their industry? Is a faster pace an itch you need to scratch or real career need?
- No worries at all, you bring up good points to consider. I know I am very lucky to be where I am, so I don’t want to forget that.
It is a give-and-take situation. I like start-ups and the potential gains, the pace, etc. I hate start-ups because of the risks and potential poor WLB. In this chapter of my life, a start-up is inconsistent with my family goals. Divorce lawyers are too expensive, lol.
If you are the only lawyer, you will be de facto GC and wearing all hats. Except to be involved in much more than just contracts, whether because you are asked or by necessity because they have no idea what they are doing.
I’ve done it and loved it. It was a great opportunity to learn new areas of law outside of my wheelhouse, learn business, and get real world experience with contracts. In my case, the workload was WAY less than in BigLaw but your mileage may vary.
I took the leap in a similar situation and enjoy the role, but as someone else mentioned, be prepared to be a defacto GC without the GC title or pay. In some ways, it is nice because you do get exposure to lots of different areas if that is something that interests you, but being a one-man show can be stressful. It's hard to take true undisturbed time off when there is no one else the biz can go to in your absence. Make sure you ask about budget for outside counsel, tools/CLEs, and get a feel for how the executives view legal (i.e. Do they want a 'yes man' or do they see legal as an equal partner?).
- Thank you. Before you accepted the role, did they say you might have to take on some of the more GC roles and responsibilities?
  - They did and it was also something I wanted and asked about. TBH I am kind of burned out on commercial contracts and I did not want it to be 100% of my role, so this was a good move.
I’ve done this before (for about a year until the company was acquired). You can do it! It’s great experience, actually. In addition to your outside counsel budget, I would ask who you would report to, who your internal clients will be, whether there is a path to a general counsel title.