Your second startup is just as likely to fail as your first—only in dumber, more frustrating ways. You think you’ve learned. You think you’re smarter this time. And that’s exactly why you’re about to overcorrect yourself into oblivion. Almost twenty years ago, I first read The Mythical Man-Month, and learned about the concept of the second system syndrome. I’d like to believe it helped me avoid some mistakes as a coder. However, with time, I’ve realized there’s a wider-ranging issue that happens at a higher altitude. More than merely the systems themselves, people bring with them different baggage depending on whether this is their first rodeo or the second. And that baggage can make all the difference.
The Pendulum Swings
No matter whether your previous startup was successful or not, you likely have a bunch of learnings that you’d like to implement. That’s great. Things get problematic when we obsess over not repeating past mistakes to the point where we wildly overcorrect. You spent years hating micromanagement, so now you ‘empower’ your team to the point of utter chaos. Congrats, you’ve gone from toxic control freak to absentee landlord. The pendulum keeps swinging, and your startup is the casualty.
Anything taken to an extreme is probably not healthy for your startup. You cannot George Costanza it and aim to do the opposite of everything you did last time. Balance isn’t something you find—it’s something you fight for.
The founders who get it right aren’t the ones who blindly avoid past mistakes. They’re the ones who see their own biases in real time and resist the urge to swing too far.
The Doing-It-Right Trap
When we do things for the second time, we might think we can see ahead some of the mistakes that will come up and tackle them preemptively. However, that very easily can turn into an over-engineering-fest. I’ve stopped counting the startups I saw that spun up dozens of micro-services within their first few months because their previous system was a monolith for too long. First-time founders ship garbage because they move too fast. Second-time founders build intricate, over-engineered masterpieces that never leave the garage. Stop designing an architecture to handle a million users when you don’t even have ten.
Just because last time you rushed into implementation too fast instead of focusing on business needs, that doesn’t mean that it makes sense to pass almost an entire year without having written any code because you’re still “defining your ‘unique value proposition.’” Again, balance is everything, and you’re going to be making mistakes. Some early-stage startup “mistakes” are actually vital tradeoffs that enterprises make to achieve vitality.
Naïveté of First-Timers
All this said, I still feel the need to stress the value of experience. Having done something once is almost always an advantage—if you don’t waste it. Some founders treat startup pain like a hazing ritual—‘You have to go through it.’ No, you don’t. You’re not getting a badge for struggling through preventable disasters. Skip the obvious landmines so you can step on more interesting ones.
Ideally, companies should be making different types of mistakes entirely. So, having the pendulum swing between hiring too many juniors and not hiring juniors at all is the same kind of mistake. Learning here would be avoiding pitfall entirely (your second time or even the first time), to focus on different decisions. Sometimes, doing things “the hard way” doesn’t really make sense.
I recently heard about a senior executive at a unicorn startup who admitted to not knowing how to formulate their strategy. A crucial process where even minor improvements could be worth millions of dollars in value. However, the decision there was to do things internally—knowing they lack the skills—for short-term gains. This naivety leads many companies to avoid their edge.
Make Smarter Mistakes
As always, the right solution requires finding the middle ground. You cannot aim to make no mistakes because that will likely lead you to overcorrect previous ones. Look to make no dumb mistakes in the same areas. Instead of trying to avoid risk, manage it better based on your learning.
Look, you will screw up. The question is: Will it be an avoidable mistake or an interesting one? If you’re too deep inside your own head, it’s time to bring in people who’ve seen more than two startups’ worth of mistakes. I’m here if you want to stop making rookie errors in a veteran body.