A lot is different.
No illusions about fundraising and your relationships with Venture Capital.
You go eyes wide open - Every VC wants your business to be the 100x returning company. A $100M exit could be life changing money for a founder but for a Series A investor that may not even be 2x. That math doesn't work out for their fund returns. Having clarity about the VC math helps you align your aspirations with their spreadsheet modeling.
A stoic attitude towards the highs and lows
Startups are a rollercoaster. One moment you are top of the world and the next moment you are down in the dumps. The self-doubt and the imposter syndrome doesn’t go away even when you are doing it the second time. But having been through the grind once, you know nothing lasts forever. You know deals will fall through, employees will leave, there will be 50 no before you see a yes, and there will be days you would want to quit. But you are able to weather a lot of it, unfazed.
Knowing what to say no to
Having seen so much, you develop a strong instinct on how many things are going to pan out. It becomes easier to say no to many things so that you can prioritize what really matters. When you are doing it for the first time, the only way to know if it would work is to try it out, that’s not the case second time around. But this is a double-edged sword.
Instinctively saying "no, I've seen this, it doesn't work" might be right 70-80% of the time, but you risk missing those 20-30% of opportunities that could work this time around or in a different context. The key is to be mindful about it.
It’s a marathon not a sprint
First time around, your sense of company building isn’t formed, so you mostly optimize for the short term. 90% of the startups fail within the first few years - so why think long term? Second time around, it’s different. True, your company’s odds of survival are still low but you are not building the company with the mindset of “what if we don’t survive” but “what if we do become hugely successful” - what are the things I would wish at that time I had taken care of earlier?
Awareness of where you need help
The years of imposter syndrome ensures you are acutely aware of your weaknesses. Hence you seek out people for help. The best thing a founder can do is to surround themselves with people that help them navigate their blindspots. This also includes having people who can just be emotionally available for you - startup building is hard and lonely, founders need all the help they can get.
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