13 Lessons from Andy Rachleff (Co-Founder @ Benchmark)

Andy Rachleff is the co-founder of Benchmark, one of the most-respected venture capital funds. He also founded and is now the chairman of Wealthfront, a personal finance tool used by millions of customers.


Andy is the rare case of a person that has achieved the top 1% of success in both the investing world and the startup world, and he has loads of wisdom to share with the world.


Here are some of the top takeaways from studying Andy and his career.

Andy Rachleff (Benchmark)

Lessons from Andy Rachleff

  • When hiring, look for drive over skillset. Skills can be taught or trained, but mindset and passion cannot.


  • Value intellectual curiosity over every other trait. The moment that you stop loving to learn is the moment that you plateau. The best entrepreneurs and investors are constantly looking for answers to their own questions.


  • In order to recruit the best candidates, you need to create fear that if they say “no”, they are going to lose the chance the chance to join. This is a part of good storytelling that isn’t talked about enough. If you want to influence people, you have to make them scared of the idea of missing out.


  • A board member who tries to tell management what to do is a pain; a board member asking questions to ensure management is intellectually honest is a valuable. Nobody likes being told what to do. People like arriving at the answer themselves. Good board members let founders arrive at that answer without interference.Β 


  • The only way to make money is to be right and non-consensus. This seems to be forgotten today where everybody wants to be politically correct and not say the wrong thing. Money doesn’t care about any of that, and it rewards those that don’t follow the herd.


  • You want products that are bought, not sold. All software companies today aim to be a product-led growth company. You want the market pull to outweigh the company push for product adoption.


β€œI believe the market is always right, and the market knows a lot better than any of us.”

"Always put the gun in the other person’s hand. If they shoot you, just don’t work with them anymore."

"Create a fear of loss because fear of loss is a much greater motivator than the joy of gain.”

"If the customers pull the product out of your hands, you don't have to be that great at operating."

"It's better to amplify the things you're good at than fix the things you're bad at."

"You learn more professionally from success. You learn more personally from failure."

β€œWhat do you uniquely offer that people desperately want?”

One Place to Learn the Different Parts of Venture Capital

We started our careers in venture. After about a week, we had a realization.


We had no idea what we were doing.


Turns out, we weren’t alone.


Junior VCs don’t get training. You’re forced to figure it out on your own.


Learning the rules, tools, and players takes FOREVER to learn. That’s why we made the ultimate VC resource library to speed up the learning curve.


Confluence.VC Resource Library

Our best VC resources … FREE