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The Hardest Part of Running a Startup Isn’t What I Thought It Would Be


Before I had started working at a startup, if you had asked me what I thought the hardest part would be, I’d have probably said the long hours, technical unknowns and not always knowing if you still have a paycheck.

While those are all absolutely valid concerns, they aren’t even close to the toughest part.

As I mentioned in a previous post, I am the co-founder and CTO of a tiny startup called Mass Mosaic. We are a three-person team, and I’m lucky enough to have two great co-founders that really embrace the idea of collaboration and trust.

As start-ups go, I’m pretty lucky. Great team, great product that will hopefully actually improve people’s lives. I’m respected not just as a code jockey, but as a true partner. The only thing we’re missing is money.

Everybody wants to grow their business, but when you have a great product and don’t have (a lot of | any) money, there is a sense of urgency and frustration that can come with it. When you have a tiny team and no money, this can sometimes be amplified, since everyone on the team is already pulling triple-duty.

Whether you’re looking to get some angel-funding, hoping to get picked up by a crazy VC who wants to throw buckets of cash at you, or are just trying to bootstrap your way out of eating ramen for breakfast, lunch and dinner, time is the one thing you have less of than money.

This means prioritizing tasks becomes critically important, and also seemingly impossible. You simply don’t have enough bodies to do all of the work that needs to be done, so you have to be vigilant about making sure the stuff you’re working on really is the stuff that will get you the most bang for your buck.

But what’s the right bang to be focusing on? User acquisition is usually an easy metric to use, at least to start with. So you’ll find yourself in a position where you can take two weeks developing something new that will hopefully give your user acquisition numbers a kick in the ass, or you can spend those two weeks making your product even better for the existing users.

This is a much harder decision than it seems. At least so much harder than I imagined it would be.

Logically, I know that we need users. Without user growth, we will not get angel, VC or bootstrapping money. But logging into  our own product and seeing how thrown-together the edit profile area looks makes me crazy. Knowing the awesome features I could be building for our users versus working on the moonshot for two weeks is harder than I thought it would be, because I care about having a product I’m proud of, and that people fall in love with. And having a smooth user experience matters for user retention and .. and.. AND… !!!!

Even when you’ve made peace with the fact that the next set of UX improvements or slick features simply has to wait because you need to focus on user acquisition, knowing which tactic to work on to get there can be almost as hard. [tweetable]Two weeks is a long time in un-funded start-up land. [/tweetable]

You can (and should) do research to see how other start-ups got their first 100k users, but you also need to realize that everybody else with a startup is reading those articles too, and so those tactics might be played out already. Or they just might not be a good fit for your product. Maybe Facebook isn’t the right place to launch your new app for rating dildo battery life. (Or maybe it is.)

There are dozens of ways (and exponentially more variations) to acquire users. Which one is right for your product? Which is the easiest to implement? Which one is the highest risk but potentially the highest reward? Which one lets you sleep at night knowing you didn’t do anything sleazy? Which one will let you start to see whether or not it’s working as quickly as possible? Which of the things I just said is the most important to you?

[tweetable]At some point, you have to put on your big-girl panties and make a decision.[/tweetable] Yes, it will be an MVP version. Yes, it’s partially designed to test user engagement and interest. But two weeks is an eternity in tiny start-up land. Larger companies may spend weeks with dedicated teams of people just coming up with the ideas, then another few weeks making a decision, and then potentially months executing it. When you’re small, you just don’t have that kind of time.

[tweetable]For me, the hardest part about running a start-up isn’t the tech. It’s not even failure.[/tweetable] I am a believer in the “fail fast” model, and I think that if you haven’t failed, you’re not stepping outside your comfort zone enough. But having the confidence to believe that spending our most precious commodity, time, on something that may net zero results is still worth trying? That’s challenging. It’s not so much about failing, it’s about failing while literally every moment really counts.

About the author


I'm a tech nerd from NY/CA now living in Lisbon, Portugal. I run Grokability, Inc, and run several open source projects, including Snipe-IT Asset Management. Tweet at me @snipeyhead, skeet me at, or read more...

By snipe
Snipe.Net Geeky, sweary things.

About Me

I'm a tech nerd from NY/CA now living in Lisbon, Portugal. I run Grokability, Inc, and run several open source projects, including Snipe-IT Asset Management. Tweet at me @snipeyhead, skeet me at, or read more...

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