Ask HN: Navigating Startup Growing Pains Situation

>>On the otherhand, I know I would resent the technical cofounder receiving an enormous financial benefit from developing a non-viable disaster from which the company needs to be rescued.

If the technical cofounder created a working prototype that allowed the company to achieve certain milestones (e.g. paying customers, seed funding) then I'm not sure why you'd be resentful because it seems the (initial) job was accomplished.

You rightly point out that you bring a valuable contribution to the table, but it seems you might (possibly) be underestimating how capable and determined the founders (and their investor network) will be able to source somebody else to rearchitect the platform.

If you're one of the few luminaries in your niche, then feel free to start negotiating for a large compensation package that includes serious equity or favourable provisions. If on the other hand you feel that there could be others that could rearchitect on a "good enough" basis at a (potentially) lower compensation price point, then perhaps you might want to lower your expectations walking into the initial negotiation.

Either way, it intuitively feels that your expected negative emotional resentment is not the right frame to start evaluating the possibilities around this opportunity.

Thank you for the thoughtful reply. I had similar thoughts of my own, but your own perspective was helpful for my reflection.

I have been in similar shoes, and had a huge impact as a founding engineer (#2 employee) at a startup (now unicorn). I wouldn’t say I had tremendous niche skills, it’s more that I took so much direct ownership and accountability of so many problems that I was able to have outsized impact for the first few years until the company became too large for me to keep track of all of it (many years later). The founder knew my personality traits (we worked closely before) and chased me very hard in the hiring process.

Many new employees and customers would ask me, after seeing me operate: “Why aren’t you the CTO and the founder is, since you are the de-facto technical authority here of every system?”.

I had a successful career at that company but I never really brushed off the exact resentment you talk about, so if I were to do it again I don’t know if I would. It was a very hard emotion to deal with.

You build something great one day or enable a massive new customer deal, get a rush of endorphins because you single-handedly made it happen via heroic efforts, then you remember your financial outcome will be a tiny fraction of the founder’s. My equity will be valued at best ~$10M (or more likely the ~$2M I already cashed out and the rest $0, we’ll see if they survive this downturn), whereas the founder will easily take $1B+ from this (and has already cashed out $xyzM).

These days I’m generally “happier” at FAANG being a good team player and just helping everyone around without a “grandiose” mentality, I am at peace with being a small cog in a large machine. I don’t think I will ever do a startup as a non-founder again, I don’t want that feeling to surface ever again.

From a cursory read, it seems like you may be in for a similar path with similar inner demons.

Thank you for sharing your story. It definitely resonated with my own imagination for how things might go.

I have my own conflicts regarding what size of role I want to play. Being the humble small person is typically the area I operate in. I also know the rush and miss it. The distinct lack of importance from my current role has been a source of great inner turmoil for a several months now. But its also so very easy for me to see how the chase could lead me seriously astray.

For now, it has been good motivation to create some things in my own time which has been fulfilling in its own way. Not sure what the future holds at this point, but again thank you for sharing.

The most challenging part about any startup is NOT the technology it's building but finding product market fit.

The company did all the work to discover that, and what's stopping them from finding someone else to build it? Why does it have to be you?

Unless the niche expertise is impossible to find elsewhere, this ^^ is dead on right. Other comments encouraging the OP to build their own company now and apply to accelerators is a short sighted view of how hard it is to build an actual company and the many things besides he tech that it takes.

> How do I negotiate a situation where I can receive the value of what I provide?

This is a good question. But before you find the answer, you have to drop the resentment. Other commenters have covered why, but if you cannot get past that, this role is not for you.

You also need to accept two important truths:

1) The success of a business is about far more than the elegance of its tech stack.

2) Your ability to re-architect a platform is not unique.

Focus on your own correlated truths:

1) The operational optimization of a business is correlated to the elegance of its tech stack.

2) Your background will make it an easier road to walk to re-architect vs. people without your background.

In short, come in showing them that you offer value above others and can help them succeed. But do not walk in as a prima donna acting like you are their one and only savior. Ask for compensation that makes the work worth it to you, but don't begrudge them their own success.

After being both a technical cofounder and a senior brought in for an MVP rewrite at different points in my career, I completely echo @codingdave’s opinion. Unless it’s the 1940s and you’re recruiting for the Manhattan Project, skill sets are not as rare as we engineers like to think.

Assuming you want the job, the goal is not only to demonstrate the value you can provide, but also the ability to build a good working relationship with the founding engineer. Regardless of his or her shortcomings, the founders will be loyal (to a point) simply because they got them this far.

Prove you have the expertise to evolve the system, but also that you can be a team player. The combination of these two traits is really what’s rare; either in isolation is comparatively common. Business stakeholders can’t really tell the difference between a mediocre engineer and an outstanding one; they can only judge their communication skills.

Whatever you decide, keep in mind that both issues—rearchitecting the product and learning to partner with its original author—present enormous opportunities for growth. It’s a rare job where you know what the challenges are going in.

Lastly, should you get an offer, make sure the salary is one you’re happy with. Equity is a lottery ticket that can be diluted or invalidated at any time. Don’t count on it.

You are potentially being hired to solve a different problem than the founder at a significantly lower personal and professional risk to do so. There's nothing to be resentful of.

But I say potentially because if they find this you will probably be rejected as an applicant. This is a major red flag to any hiring manager.

With your expertise and the fact that they're so early, you should be able to build a competing business with your superior product right?

Then you can keep all the rewards (and find out all they had to do to be in the position to be able to hire you).

Sounds like a win-win, you should be talking to startup accelerators not startups hiring.

Sounds more like a potential lawsuit to me.

Exactly.

Start your own company.