Hi and welcome to the A16Z podcast. This conversation between Bethany Coates, CEO and founder of

Breakline and Andy Rackleff, co-founder and executive chairman of Wealthfront and also co-founder of

Benchmark Capital, is based on an event at the Breakline Tech Program for Military Veterans, which was

hosted at Andresen Horowitz. In it, Coates and Rackleff talk about what it's like

to go from being an investor to a CEO, the enduring importance of product market fit, and other

key elements of good leadership as an entrepreneur. So, Andy, one of the things that I've reflected

on quite a bit about your journey is that you invested in many promising companies over many, many

years. You could have ridden off into the sunset 12 years ago and just put your feet up.

And instead, you decided to co-found wealth front. And so you went from being an investor now

to being an entrepreneur and a CEO. You have said many times

that if you had known how difficult it would be to start and build wealth front and to run it,

you wouldn't have done it. What has been so hard about it? Oh, God. People are difficult.

You've all led people and you all know how challenging that can be.

It's a lot easier to think of the solution than to actually execute it.

And I think that perhaps is the most difficult part of the entire process.

Has it been difficult in different ways as you build the company?

So basically what we're trying to do is take the financial services that are delivered

to the very wealthy through people called private wealth managers, automate those services

and software so we can deliver it for account minimums of as low as $500, and deliver better outcomes than what Goldman

Sachs gives you with a $15 million account.

That's because almost everything in investing that's good practice is really routine, and

computers are a lot better at routine things than people. So one of the challenges is that the industry

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