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Dalton Caldwell on Lennys Podcast

Dalton Caldwell on Lennys Podcast

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Dalton's Background

So Dalton is a partner at Y combinator and I love him because he speaks extremely simply and clearly. A lot of his advice is just common sense but it is refreshing hearing that from one of the most successful VC partners in the world.

A good example is when Lenny asked him for a recommendation of a sales book, he just recommended to read the number one sales books on Amazon like Getting to Yes or FoundingSales.

Here are the key things that stood out to me in the episode

  • The Collison Install
  • Founder Conviction
  • Everyone experiences a moment where all hope is lost
  • Meet with customers 20-30% of the time

The Collison Install

Collison Install Quote

The "Collison Install," named after Patrick Collison, co-founder of Stripe, is a notable tactic used in the early days of Stripe to ensure customer activation and retention. This method involved the founders personally visiting potential customers to help them integrate Stripe into their websites.

The Collison Install involved a hands-on approach by the Stripe founders, who would visit potential customers under the pretense of being in the area and offer to help set up Stripe on their websites. This proactive approach not only ensured that the Stripe integration was completed but also helped overcome inertia or technical hurdles that customers might have faced.

Founder Conviction

Dalton Quote

This quote stands out for me because Dalton does not speak like Tony Robbins often, he is a clear and simple talker and so for him to be saying this so emphatically really shows that determination and willpower are such key factors in success.

Dalton Quote

The Quote Continues

"They just believe and it's almost like that internal gravitational force inside of them is so large it kind of warps the world to bend to that will and people start to believe it because they believe it so much and they convince their employees to believe it and they convince everyone around them that this is going to happen for them."

I wanted to write that out in full measure as I think it takes time to really ponder and consider that statement. It's an interesting level of convinction isn't it and I suppose you have to believe things to the magnitude that the people is talking about do in order to build the likes of Airbnb and Stripe.

Everyone experiences a moment where all hope is lost

Dalton Quote

This is inspiring. It shows that in the worst moments you have to find a way to keep going. Take stock, keep in the fight. Consider your options, try something else, just stay in the fight. If every single company goes through this, then you can take comfort in the fact that you are not alone.

For more on this read Don't Die by Paul Graham

Meeting with customers 20% of the time

Dalton Quote

I really like this because he lays down the challenge of specifically making these in person as much as possible, so that you are talking and showcasing your product. Combine this with the Collison method of conveniently making yourself available!

What was personally motivating to me

He talked about ERPS being a request for startups that YC has done. This is a space that we work in, it's made me want to do a deep dive and consider what sort of tools we could do.

The other thing was he talked about the glue that stitches enterprises together and the products that are out there that could help with this. Again there is lot's to consider for us as that is exactly what we do for companies!

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