Create your second opportunities

In 2013 YCombinator, the world's largest startup accelerator, selected my startup to have an interview. After hundreds of hours of preparation, there we were in a room with true titans of Silicon Valley: Paul Buchheit (creator of Gmail), Geoff Ralston (Yahoo! Mail), Michael Seibel (Twitch), and Kevin Hale (Wufoo). It was only 15 minutes. 15 minutes where you put it all on the line with the most far-fetched and tough questions. And we failed. We got rejected, but it wasn't the end.

Failure is normal. As bigger the challenge is, the more atypical the success. We always hear that we learn from our mistakes and that we will do better next time. We often believe that we will never get a second chance because it is not part of the script, but that is not true. Most of the time we just have to ask for a second chance by being humble and making a good argument. And that's what we did.

The night we were rejected, I wrote an email of 950 words (this post has 530) where I clearly and forcefully attacked their fears and doubts, always with a lot of respect. They gave us a second chance the next day. We were able to have another interview and demonstrate again the value of our project. We were not accepted, but we left there with the total certainty that we had done everything in our power. We really did.

Don't wait for a second opportunity. Create it!

With this post I wanted to share with you some tips that has worked for me countless times to get second chances, the vast majority with a happy ending. It doesn't matter if you ask for a second chance by email or in a face-to-face conversation.

Appreciate the time our interlocutors are investing in the process.
Accept their decision. This is not a debate, the decision was made correctly with all the information that was available. They have not made a mistake because we have not been able to share all the evidence and information of value with them.
Use a maximum of 3 high-value reasons. Try to find the most memorable. You can also choose those that were unclear or generated insecurities for your interlocutor.
Always provide data and evidence, not beliefs, assumptions, or phrases that do not help to quantify. It is always better to use numbers and percentages (even if they are approximate) than words like "almost always", "many", etc.
Be humble but confident. This should not become an inspirational and grandiloquent speech or a vendetta. It is a tool that helps to resolve ignorance, prejudices, fears, or misunderstandings.
Be grateful for the opportunity to have a conversation even if the result is not the expected.
Never push too hard. Making the other person feel uncomfortable may awaken the feeling of running away and want to cut ties with you as soon as possible.
But the most important, ask for that second opportunity.

If this worked with the most demanding business accelerator in the world, I am sure it will also work for you in thousands of other situations.