My startup crossed $2M/yr and now co-founder is going for a power grab

34 points by potluckdinner ↗ HN
So 3 years ago, me and 4 guys start a company. Roles are as follow: CEO COO Chief Development Officer Chief UX officer (CUXO) Chief Data officer (Me)

Everyone is 20% owner.

Currently my team has 9 people. Chief UX officer team is 3 people. Total company is about 17 people.

Our business model is basically...we collect publicly available data, clean, normalize, and enriched with other data sources. The data is made available via an API as well as front end.

I basically architected the entire backend infrastructure that manages all of our data pipelines as well as was significantly involved in development of the models/algorithms for enriching data. Chief Development Officer helped out with some execution in early stages.

Chief UX officer was responsible for front end. He also manages the API operations after we publish data to the db he manages.

During formation, ~3 years ago, we agreed no one would have the role of CTO. About a year or so after formation, CUXO said he wanted his title to be changed to CTO. Chief Dev Officer and I strongly opposed this and with the support of CEO, we decided that there was no need to change things from what we had originally agreed on.

Chief Development Officer left the company about a year ago and all his responsibilities fell on me. Though tbh, he wasn't doing much since I had hired a team of offshore engineers.

(Today)

CUXO is the last person to quit his job and go full time. We had a meeting this morning and he said that He wants to change his title to CTO when he starts next month. His stated reasoning was pretty silly to be honest, He said that he wanted the title because it would be better for his career after the startup - which to me is probably the least compelling reason possible.

CEO and COO said that didn't want to get involved and it was for me and CUXO to sort it out ourselves.

I'm planning on having a meeting 1:1 with him this weekend and explaining that I think the role of CTO implies a set of responsibilities far broader than would be appropriate for either of us since we've kept a very sharp line between front end and back end in terms of management. I think him being CTO will also cause confusion with regards to our roles in the company, both internally with our respective teams and externally when we have client meetings.

I also feel like I've built an extremely sophisticated back end system on a pretty unbelievable budget...and having him as the CTO I feel would massively undermine the work that I've done.

Lastly, I don't like the idea of us trying to go back and change the original agreement. We all decided on equal equity (20%) as well as no CTO because we wanted to make sure everyone felt equal.

Aside from the fact that I don't think he deserves the role of CTO, I really don't like the idea of us re-negotiating the terms of the business formation. Suppose he gets the CTO role, will he later come back and argue for more equity?

I should also mention that the first time he asked to be CTO, he said he deserved it because he setup the slack and gmail instances so that makes him CTO. This indicates to me that he is fundamentally unrealistic in his outlook. Also combined with the fact that our relationship has always been a bit tense, I expect him to react very negatively to me opposing his title change.

Another important piece of information is that the CEO and CUXO are old friends which I think might be impacting his desire to avoid getting involved in this.

I often read about startups failing because of disagreements with co-founders, and I'm really concerned that this could become a much bigger deal than it should be depending on how insistent the CUXO is. I strongly object to him taking this role and I feel like he strongly feels he deserves it.

Does anyone have any advice they can give on how I should proceed?

63 comments

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Lawyer. Keep them on a short leash, they can fuck it up. At the very least consult one and pay for it up front not in arrears to some subsequent drama. Possibly even use a disposable good lawyer to avoid being over amped. If they know there's no subsequent business they may be more dispassionate.

It may be impossible to remain amicable once you lawyer up. Using "I saw a lawyer" or "I am seeing a lawyer" as a weapon won't help you.

Have you thought about a formal external mediator? Doesn't have to be a lawyer, could be interesting to facilitate the difference between you.

People want different things in life. Sometimes the differences are irreconcilable.

Do you have VC funding who you could discuss this with? Do you have a mentor? You probably need somebody in the business space who can advise you f2f not randoms online.

Not me. I tried to help a friend (at his request) in a situation around IPR and I fucked it up, he isn't a friend any more and nor is the other party. Don't want to be that guy ever again.

I think that's basically the nuclear option that I really want to avoid. I think it would cause irreparable damage to the group especially at this moment where it's very possible the company is about to significantly increase in value.

To be clear, I haven't had a talk with CUXO yet, so maybe I'll just explain my reasoning and he'll accept it. However, I don't feel like that's likely.

It's hard to explain but I feel like he's been planning this move for some time now. Little things, like inserting himself in some of my teams communications and insisting on us publishing final data to his db.

Unleashing your lawyer on him or the company would be the nuclear option, consulting one to know your options is fairly standard, if you don’t yet know how things could be (and I am assuming you don’t since you are asking on HN).

There are a lots of people who will always try to push a bit at the margin for their own benefits, and when it happens you can either yield, push back or stand firm. From your post it seems you want to stand firm, and exploring all the possibilities and rights you have will clear your mind on the next step. Short of you waiving all your rights, there are actually very few things that could happen in these kind of situation

I basically agree with this. Seek council, but do not weaponise it. Understand your (legal, moral, ethical) rights, and defend them.

Good luck.

Obviously based on my own prior experience in a mildly analogous space, I agree to its nuclear consequences/effects introducing third parties of any kind.

Some of what you say goes to a loss of trust and full disclosure to motivation and intent between you which is sad, but alas also very normal.

But I do suggest you at least seek advise from somebody you pay, to advocate to you, privately of what is normal and also necessary here.

I'm not sure what new advice a lawyer could give since we sort of already went through this last year when we bought out the Chief Dev Officers equity. Maybe I'm wrong, but I feel like I have a solid understanding of what our contract entitles us to. My main concerns are basically navigating this without dirupting the team dynamic as well as guarding against future attempts from CUXO to get power in the org.
(comment deleted)
A good title to help further his career seems like a valid concern (even if the title itself may not be legitimate), but so are your concerns.

You could put the burden of finding a solution on him? Share your concerns - that you did the bulk of back-end technical work, and feel that giving someone else the CTO title would devalue it. If he can find a way to get a better title (CTO or something else) without devaluing other roles, then you would not object. Since he's the one that wants to change things, it seems fair that he come up with a solution.

> A good title to help further his career seems like a valid concern

Not for the business.

Like others have said it’s at least the CEO’s role to work it out and if they said it’s not their problem then there are bigger concerns.

It's also important to consider that in a future interview, they are going to ask "tell me about your time as CTO at ExectuiveSuitDramaCorp?"

So it's not just going to be just a title. Responsibilities will shift towards the title. It is very much a power grab, and if they do not have the power, then that title will hurt them in the future.

Appreciate the reply.

I think this is probably the best approach, however I find it hard to believe there is a possible title that he could suggest that wouldn't similarly undermine me somehow.

I'm trying to avoid the conversation turning into an argument about whose done what for the company because I think it would irreparably harm our already tense working relationship, however I think without a doubt I have overwhelmingly been responsible for the companies success from a CTO perspective, especially since taking over the responsibilities of the former Chief Dev Officer. So much so, during client calls I'm often introduced as the CTO by our CEO. CUXO has had practically zero client interactions since he has so far not been working full time for the company.

Would CUXO be happy as Chief Product Officer? The whole thing sounds pretty silly, but if you want to be CTO, then CPO seems like a reasonable thing to offer CUXO (if you think he’s any good at product stuff, anyway).
If the CUXO is not a narcissist and does take the companies interest into account, this is probably the most cogent idea in the thread.

CUXO is obviously a ridiculous title as are both CDO titles.

Yeah this seems to make sense. You should have a CTO and CPO is also logical. If your startup is growing fast you should be changing the structure regularly and be ready to adapt to the change.
> So much so, during client calls I'm often introduced as the CTO by our CEO.

Sounds like you are already doing most of the CTO work and virtually getting recognized as such. Step up and claim the CTO position.

You have to weigh your personal benefit, against the benefit of keeping the company running somewhat smoothly (which is also in your interest). Assuming titles don't affect your current salary/equity in the company (you can get this in writing), it is only your future job prospects that are affected. The CUXO is probably (perhaps rightfully) worried his title sounds too unserious, and wants a better safeguard.

That said, changing the deal you had all agreed to at the start also makes working together harder. Instead of focusing on the company, you find yourselves also fighting among each-other, since the clear lines you had drawn up at the start are apparently up for negotiation. Good fences make good neighbors, as they say.

Note that I have no experience in such matters, I can only offer a fresh, hopefully clear, perspective. Good luck.

> CEO and COO said that didn't want to get involved and it was for me and CUXO to sort it out ourselves.

uhm, no. CEO's job is to run the company and this is tearing it apart. he cannot shirk this responsibility.

very sorry you are running into this situation. sounds like the 5 of you were NOT full time up til recently? i would suggest recapitalizing the company if possible (i have no idea how this works) since your nonfunctional CDO probably has a chunk of the company in exchange for not doing much.

I went full time first about 2 years ago. Since then the remaining members have gone full time one by one with the CUXO being the last to go full time scheduled for July 1st.

CDO was bought out last year with his equity being distributed evenly.

>uhm, no. CEO's job is to run the company and this is tearing it apart. he cannot shirk this responsibility.

Yes, I agree. I'm hoping to resolve with without needing him to come in to mediate but it feels unavoidable and I think it will ultimately cause harm to the group. I'm also concerned because I feel like I need to start actively guarding against the CUXO from trying to encroach on my area in an attempt to assert himself as a "leader"

"CEO and COO said that didn't want to get involved and it was for me and CUXO to sort it out ourselves." That's a bad CEO.
This is why contracts exist. I hope the agreements you listed are written down.
Everyone should be “Co-CTO”
How about Co-CEO? Just go all the way. Chief Everything Officer.
You should fire this person, and do the startup with the rest of them. If the other two are too weak to address the conflict, it's a very bad sign for the outcome. Probably don't need a lawyer if they aren't even full time yet. Hopefully you guys all had 4 year vesting terms so they don't actually keep 20% of common.
Is this just about titles? Can you not be CTO and he can be Chief Product Officer or something that sounds better?
Executive Senior Chief Technical Officer President
There might be another way to look at it that could be really useful in this scenario. Rather than saying that you don't want it to happen, instead, ask yourself what changes would make it so that you would be okay with the change? For example, if the CUXO was willing to sign over half of his stake (10%) to you, would you be okay with him taking the CTO title? You could argue that giving him the CTO title will give him a future leg-up in career and earnings that you should be compensated as well. If the CUXO is not okay with that, than you have a good argument for keeping things the same.
I think no one has the answer to your question. Everyone doesn't really know your team's personality and how many people agree/happy with his decision.

How about we vote on this?

Keeping good relationship and supporting partners >> Worrying so much about silly titles.
Perhaps you could be co-CTO's. Fwiw I can see not liking CUXO
Who is more replaceable? You or the cuxo?

What would happen if CUXO were to quit?

Who is more qualified to be a CTO between you and him going forward? i.e. If the company were to scale x2, x5, x10, would you or the him be able to fulfill the duty better?

Would the CEO and COO agree?

At what point do you need a dedicated CTO that is neither you or the CUXO?

How much leverage do you have over the CEO and COO? Does COO have your back?

Propose that an office of the CTO is created which would be responsible for high level technical direction and promoting technical excellence, and he could be in charge of and lead a dev or so in in that role. Jointly, a General Manager (GM) of Product Development role which reports directly to the CEO should be created, which you could step into. All development would be under that GM role, including the UX and DB teams. The product development team would be responsible for maintaining the existing product, as well as architecting new solutions and features.

If all he really wants is the title, this would give him that. Meanwhile, it gives you ownership.

I assume you are all board members also. It’s the job of the board to make sure silly stuff like this doesn’t get out of hand. Force the leadership team to make a decision.

By the way the sort of rules that dictate everyone will be equal or some title shall not be given, never last. The more you attach yourself to it, the more likely you’ll lose. Rather than sticking with “there should be no CTO”, just make the case for you being CTO.

Avoid working with people who care primarily about titles.

Is the CEO actually a CEO? I.e., does everyone else report to them? If so, they should get involved and help you resolve.

If they don’t want to, take your equity, cut your losses and move on.

It sounds like OP cares just as much about titles as the guy who wants to be CTO, tho.
maybe he's just seen the Blackberry movie and now getting new ideas, prepare for a rough landing
There is no such thing as 4 people "equally" running a company, even if the equity is equally split, precisely to avoid these types of situations. If a majority of you (or whatever your charter says) are unhappy with the CEO, then you can change the CEO, but until then, someone needs to ultimately make decisions. Who do the two of you report to? Who is in charge? That person needs to figure this out.

I'd also ask everyone in the room: What's in the best interest of the business?

1) If it’s not immediately clear who should have a CTO title and why, no one should have it. Would also think you should consider for no one to have a C-suite title except for the CEO with such a small team. You’ll need those titles to be available for when it matters for the company (it doesn’t yet).

2) The CEO needs to make the CTO decision for their team. They can take recommendations or arguments, but they can’t let this org structure problem fall to the team they manage.

> CEO and COO said that didn't want to get involved and it was for me and CUXO to sort it out ourselves.

It seems like they're sending you a signal that the CUXO's argument has at least some merit. Last time they were aligned with you and this time they're telling you to sort it out yourself. Ask the CEO and COO is they have some feedback for you that they're holding back on.

The first backend developer is customarily the CTO. UX simply does not involve integrating as many systems. He doesn’t understand it and that makes him even less qualified. He’s a CPO at best.
1st, congrats on $2M/yr accomplishment. Very few ever make it to that level, and far fewer do that in just 3-years.

——-

Some questions that might better influence someone’s response to you:

- Why did two founders recently quit?

- How is that 40% equity being handled (did they take the equity with them)?

- If the 2 departed founders didn’t take equity with them, do you now have 1/3 voting shares? (Since there’s only 3 founders left)

- Do you feel you deserve the CTO title?

- Why do so many people in the company want CTO title? What does CTO title represent to people?

- why do people care about titles when there’s only 17 employees (no intended disrespect with this question)?

This sounds like it's ripe for the you-cut-I-pick process.

Ask him how much equity he would give up in order to have the CTO title. Then after he says how much he thinks the title is worth, you get to pick whether you give up the equity (to him) and get to be CTO, or whether he gets to be CTO but you get a piece of his equity.