Is my startup about to fall apart?

[zak833]

I'm involved in an online dating startup with one other cofounder and it has the interest of a prominent angel investor who is willing to pull the trigger with a full-time CTO on board (we are both mostly non-technical). 1.5 months in, and communication issues are beginning to surface (we didn't know each other that well before forming the company.) Although I know he is invested in the company/adds a lot of value, he maintains a consulting gig on the side to pay the bills, and he is very particular about how he divides his time between the two commitments. Whether it's for this or other reasons, he occasionally falls off the map (sometimes for days at a time) and doesn't pick up 99% of my calls first time around. Having said all this, he has been meeting his deliverables and progress on the company is being made.

At this point, I've sat him down twice to discuss the issue, but nothing has sunk in as there have been no improvements. My options are threefold:

a) Go solo with the project - risk him doing the same - and search for someone as a cofounder and/or CTO to build the product. I'm very into the concept but this will be a process as I'm a first-time entrepreneur, so I imagine attracting someone will be tough.

b) Give up on this project and commit full-time to another project I had been working prior to this opportunity. The other is more of a "dude business" (can easily outsource dev) which I am at least AS into as the former and I think I could learn a lot from. However, no interested investor and it's a monetized Q&A community, so probably won't have the same reach/credibility as an online dating site, assuming success in both cases.

c) Try to work out my differences with the cofounder (although it seems I already attempted this...) and try to forge a path forwards.

Any advice or feedback on this situation would be hugely appreciated.

[contagionhealth]

A startup lives in a perpetual state of 'about to fall apart.'

Sometimes you just feel it more acutely than others, based on circumstances and how emotionally volatile you are at the time, in addition to other factors like how important the issue is in terms of actual survival (yours, the startups - which are two different issues, although codependent variables).

Many more issues surface in your short post.

1. You're only 1.5 months in and you've attracted the interest of a prominent angel investor AND your cofounder is meeting his deliverables? That's doing well, not falling apart.

2. You're beginning to feel the strain. That is under your control, and only your control. Look at how you're managing yourself and your energy levels instead of just looking at the business and reaching out to potentially inflate other issues into 'startup ending' crises upon which you could then heap blame when you quit.

If it seems too tough, that's because it IS.

What you have to figure out is whether or not it is too tough for you. Do you want this kind of stress/strain/doubt to surface almost every day for the next 2-7 years?

Are you willing to continue to take on this kind of risk?

Because that's what your startup will require.

Granted, if you're lucky, passionate, and good, and you work your ass off, those will be intermittently interspersed with such blinding moments of success that you'll wonder how you could have possibly considered quitting at any point.

3. Your cofounder relationship seems to be a big potential issue for you. I take it your cofounder is perhaps slightly 'more' technical than you - but could be wrong since you don't state this explicitly.

His risk tolerance is also lower than yours, it seems, as he's maintaining a 'safety' net with the consulting gig on the side.

This can mean many things, but you should perhaps be most worried about this if you're in the CEO/#1 role, as it can indicate a cofounder's lack of trust in your ability to 'drive.'

Falling off the map can happen (I've been guilty of it), but it usually means either you're frantically busy trying to sell, raise funds, etc. or that you've got a life on the other side of the startup which would suffer if you left it, and which you're not quite ready to give up.

It's your job to find out which is going on with your cofounder, preferably before you accept funding. If he's not committed and leaves after funding, and you're nontechnical, you're in a very tricky spot.

You also don't mention the equity split, but if it's 50/50, you've got bigger issues. Maybe the cofounder wants more, maybe he or she thinks she's got 50 % of nothing. If so, it's your job to communicate (and then actually hit deliverables like sales, funding money in the bank, etc) that make the point.

4. Who is going to recruit the CTO? Does the angel know 'a few people?' Does he have a specific person in mind? If so, has he named them, shared the name and a few sentences of this person's experience, and said he'd email or call them by X?

If not, and assurances are vague at best, he's probably relying on you to find someone.

Do not discount the tremendous time, energy, and effort it takes to find this kind of executive as a first time entrepreneur.

Given the other issues, it's challenging but not impossible for you to find a CTO at this point in the company history.

5. Going solo with the project? When you're fearful of him doing the same? Not a great idea. It's a worse indicator that you don't know if he'd pursue the same project independently. That should be what you focus on tomorrow - figuring out who would keep the kids if you divorce.

6. "Another full-time project" will not help you answer whether or not the life of a startup founder is for you. Nothing you've named here (although we're operating on not much data) is a disastrous issue that would require jumping ship.

Reading through the text it sounds like you're feeling itchy, scared, and looking for justification for moving on to the next big thing, before you've even figured out if this one can work.

Side note: Don't assume success in both cases. Assume failure. Your investors will, while hoping you're different.

Not until you've explored the myriad of ways in which you can fail, and confronted these head on with users, competitors, and investors during pitch meetings (ie post launch), will you have any idea of what success and failure will mean for this company.

Work your ass off to learn what you can while working on the one you choose, and you might find a different definition of success than the one with which you began.

And you might be one of the lucky ones with 1x, 3x, etc. exits.

[zak833]

First, of all, thank you. Seriously. Second of all, here are the gaps in my narrative:

3. He is more technical than I am, and the reason he is maintaining his PHP shop is to pay the bills, whereas I am fortunate enough not to have that concern for the immediate future. This unavoidable disparity in commitment levels may have caused a bias in me as to how invested we both are.

4. We have been looking for the CTO. It has been difficult and the guy we were pinning our hopes on ultimately didn't come through. As of now we have someone who is willing to build the MVP if we pay him, and we feel he'll do a good enough job.

5. He has intimated that he will pursue the project independently. Since I really want to bring this concept to life, I may end up doing the same if we part ways.

6. I'm not sure about this last statement... The extent to which our issues pertain to the operations of the business itself is obviously important, but equally so are the overall relations between the small number of people who are trying to build it.

In general, I completely agree with your assessment of the situation, and I've suggested a call with him tonight to attempt once and for all to iron our our differences. This comment was mostly to fill you in on the details which were lacking in a post you were kind enough to respond to regardless. If you have anything to add given the new info, that would be great - if not, no worries, and thanks once again.

[Stronico]

If he's making his deliverables, then you don't have a problem you won't have with anyone else you might bring on. He probably just doesn't like phone calls and is too polite to say so. The grass will likely not be greener with someone else in that guy's place.

[scottmp10]

While I agree with the current comments for the most part, I have found communication to be a really significant part of team relations. Often, this type of problem compounds and I have seen similar situations end with a member leaving the team.

That being said, I have found that this type of issue can usually be solved by talking about what your expectations are and being clear when they are not met. Just make sure that your expectations are reasonable and leave room for error here and there.

Finally, you need to decide if you are ok with having your teammate working part time. Someone splitting their time between two projects usually contributes less than half of their potential to each team.

As others have mentioned, the fact that he has been meeting his deliverables probably means that the issue is less about contribution and more about communication. If you cannot solve the communication issues then you may want to look at alternatives without this partner.

[willheim]

Your problem is one of team building. There's you (non-technical) and a "co-founder" (some technical) who aren't really communicating with each other. We've got your side of the story but not the other's. Then there's the lack of a good CTO/technical lead. I know Y-combinator likes to have teams live and work together and that is for a very good rason: it builds the team into a unifying force!

What do you have to do? 1) Build your relationship, first. Go on a retreat together. Get a cabin somewhere, go hiking, escape life, talk, grow, code, design, build, mock, fish, cook, eat, sleep. Do not network, call, email, read news, or communicate with the outside world. Focus on yourselves and your project. Build off that energy and take it to the next level. 2) Either that succeeds or you fall apart. Lesson learned. Move on.

[dcaldwell]

A few years ago I dealt with the same issue but at that time in a different industry - resort real estate development. My suggestion is to go with a) or b). In my experience, things only get worse with business partners if they start off this well. I didn't know mine very well before entering into the deal and also confronted this person and it just didn't "sink in." That became a common occurrence. This will be a huge drain on your energy and it is better to go ahead and rip the bandaid off now than be dealing with issues down the road. I know every person and situation is different but why risk it?

[pmcconlogue]

You seem open to work and ready for input (inference based on that fact that you asked advice). He may very well not be on the same page, but I suggest taking the 16 Personalities Test and figuring out where you and he stand. Great partnerships can be found in odd pairs; don't give up.

[zak833]

Thank you so much for the responses. First time on Hacker News (came to it on a friend's recommendation...) and I'm really impressed/grateful at how engaged the advice has been.