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Ask HN: Successful tech startup but find every day emotionally challenging

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Re: Ask HN: Successful tech startup but find every day emotionally challenging

#11

Post by amorphid »

You just described my experience as a first-time CEO/founder.

One thing that helped me was getting better at expressing things in terms of what I needed & why I needed them. It was extra important to make sure the person(s) with whom I spoke understood by explaining my request back to me. I didn't always get the exact results I expected, but I usually got what I needed, or an understanding that a different might be in needed. It also helped to only request things that I really needed.

Re: Ask HN: Successful tech startup but find every day emotionally challenging

#12

Post by quickthrower2 »

sp527 wrote: post #6

It seems like the easiest way to relieve the pressure would be to hire someone to take over as CEO. Finding the right person may be hard, but you'd probably feel a lot better once you've been swapped out. You would likely want to remain in charge of product and hand off the rest of the business decisions to said person.

That's a bit like hiring someone to manage your money. Delegation not abdication. I.e. you can't sit back, relax, you need to keep an eye on their performance and how they act and behave and make sure it is in line with the company goals.

Re: Ask HN: Successful tech startup but find every day emotionally challenging

#13

Post by scottshamus »

Depends on what you are worrying about. Is it your product's future? Competitors? Keeping customers? Managing employees' performance? In my experience, stress comes from having all of these problems but not having any plan. I would write out everything that is stressing you out then try to find the highest priority. That feeling of having too much to do is a GOOD thing. It means you have tons of ideas or your customers love your product and want to improve it. That should never go away if you do your job correctly. You just need to develop strategies to know when your roadmap is full and how to manage scope/expectations. Maybe you need a Product Manager or Salesperson to handle expectations from your customers?

Re: Ask HN: Successful tech startup but find every day emotionally challenging

#15

Post by joshjkim »

it's normal and you can expect that no matter what, as CEO you'll have phases like this on/off throughout your tenure, for better/worse it is part of the job. that being said, without knowing more details, I'd venture a guess that after 2 years, you are at a size (in terms of customers, volume, team size, etc.) where you may need to start thinking about not just getting shit done, but managing your team more actively (the thing that clued me in on this beside time/revenue is "people need things from me constantly"). there's lot of resources for how best to do this, but overall it all comes down to identifying big picture goals for the business, setting clear direction for your team, identifying metrics for performance, and then allowing your people to operate relatively autonomously but have regular check-ins / reports on performance relative to the established metrics. this can be as simple as well-defined product development milestones, support tickets closed, sales number achieved, customer acquisition targets, etc. it's important to identify the correct metrics, but often times part of that process is just starting with something simple/obvious, being consistent in evaluating, and then being willing to adapt / add / modify as you and the team learn what really matters.

hope this helps, doing similar things at my company now, not easy but once I appreciated it as a new problem set it's been interesting and satisfying to work on. hit me up if you want to chat more, happy to help.

Re: Ask HN: Successful tech startup but find every day emotionally challenging

#16

Post by jamesmcintyre »

I think a leader displaying calmness, confidence and even a sort of levity towards imposing problems or struggles is very valuable even if this may be a practiced behavior or a kind of "performance" (if only in the beginning). In other words, maybe what's most valuable at any given moment is not to have all the answers for everyone in every situation but to exude an attitude which suggests "this too shall pass" and "together we'll figure it out". Over the long-haul it is likely more impactful to foster this environment and to calm those around you so that creative solutions have space to emerge instead of stirring anxiety and fear which may in turn be a hostile environment for collaboration and creativity.

I know this sounds a little idyllic or lofty and you may be thinking "yea except every day there's a problem that could actually kill our startup so I can't just act like everything's ok all the time" and this is where your role becomes uniquely challenging in that every day the sky may actually be falling, you aren't just imagining it- so how can you keep your cool?

I don't claim to know the answer but I have a feeling it involves striking a balance somewhere between being passionate, being personally invested and seeing the startup as a reflection of yourself and then on the other end centering yourself in a place of "detachment from the outcome", reminding yourself that you'll live and that "this is all just information".

I can't say I know fully how to strike that balance but this is the approach I shoot for. I think there's real power in detaching from the outcome of any given arbitrary situation- this gives space for creative solutions, rich contributions and better energy. This doesn't mean you don't care about the "success" of the startup, you can care deeply; it means you do not fear the land mines, the possible missteps because you know that these seemingly scary foes are actually bits of information, encoded information or even opportunities and that you and your team will be wise enough to see them as such and react appropriately where other's may let fear take hold and be blinded.

A book comes to mind, if you haven't already you should check it out: Antifragile by Nassim Nicholas Taleb.

Hope this helps! Remember... you got this!

Re: Ask HN: Successful tech startup but find every day emotionally challenging

#18

Post by soneca »

I am not in that position, but I have a few friends that are. My advice would for you to hire a COO - I say hire instead of promoting because I am assuming that if there were someone with the skills for the job you would already have noticed and not be feeling that much pressure.

A non-technical COO can be helpful to discuss the vision of the company and share the responsibility to execute it.

A friend of mine is Co-CEO with 2 others. It works great for them (but they know each other for some time). The key is that anyone of them can make most decisions without consulting the others.

Re: Ask HN: Successful tech startup but find every day emotionally challenging

#19

Post by princeb »

you will never feel like you will run out of things to improve on. you will never feel like it's a complete work.

what is worse is knowing that there are competitors and they are also trying to find their edge over you. you have probably between 20 to 50 different things you can choose to work on right away and there's always this nagging doubt that the projects and improvements you pick may cost you far too much and give you back far too little.

it always does feel like a hair's breadth away from failure.

i don't know how to help you. you may have great, productive employees who are 100% willing to jump off the cliff with you but at some point you will need a few good, smart, strategic guys you can bounce ideas off, who can critique, find flaws, figure out escape plans when things don't go right, and give you confidence to take on projects that may not be in your favour.

there's no formula to finding those guys. it's a tough battle. good luck!

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