A founder may need to lose credibility to build a second act

Transcript

Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.

1. 48:19

   are struggling with the second acts and you've done amazing second act work at block you did interesting stuff with blue sky interesting stuff with spiral advice to ceos trying to figure that second act out uh i don't know if i ever considered it to be like a second act it's just something that like we had what i wanted to do and i had to do and it was interesting are you're building something new it's distracting to the org and like how do you resource it well cash up was like that in the early days yeah well that's that's a good point like so i think every leader has to be comfortable with losing credibility with their stakeholders at some point in order to do something interesting like when when we we had multiple moments and these are the founding moments that um i think are are critical for a company but like we were we started with a card

2. 49:08

   reader eventually we determined that hey we should probably lend money to sellers because like no seller wants to accept credit cards what they want is to um get more sales and what helps them get more sales more capital to deploy into their business when we first brought it to our board um our board said absolutely no like you're not getting in the lending business like that's ridiculous and we lost i lost some credibility with with um you know the board and our population because we wanted to do this and we kept pushing it and pushing it eventually they said yes cash app was the same thing where we were about merchants our mission was make commerce easy and we built this thing that allowed effortless peer-to-peer as effortless is just you know sending an email to start and uh our our our coo at the time was on the founding

3. 50:00

   Team of PayPal, Keith Raboy, and even he said no. And he said, like, you know, this is a solved problem. Everyone in the company hated CashUp. It was a team of eight people and hated it for two to three years. We mentioned it less than eight times in our S1 to go public. Our investors didn't understand it at all. and every day that i allowed it to persist and defended it i lost credibility and i knew that i could earn it back if it if we saw success there and we did like we we monetized it and it became profitable and you know it's now over half our business and um so i think it's getting comfortable with like you're going to lose credibility and if you have an understanding of like how to earn that back uh it's okay and you don't have to care about like what what people think if you have the principle of why it's important and why this needs to exist and you're

4. 50:58

   okay with, yeah, people aren't going to trust me for a bit and it's okay. I'm staking part of my reputation on this and that's why I believe it. I think it makes all those answers stronger,