The Secret Art of Finding Work You Love and Funding the Life You Want | Chris Hutchins

Chris Hutchins (0:00)

I think I've gone through the exercise of what does my life cost? What do I think it would cost in an ideal version? And what do I think it will cost once I don't have kids, and once we've paid off our mortgage? And what does that need? When you don't know what the money's for, you need more.

Tyler Gardner (0:21)

Hello, friends. This is Tyler Gardner, welcoming you to another episode of Your Money Guide on the Side, where it is my job to simplify what seems complex, add nuance to what seems simple, and learn from and alongside some of the brightest minds in money, finance, and investing. So let's get started and get you one step closer to where you need to be. Today's guest is someone I've been looking forward to having on the show for a while now, as whenever I Google just about anything worth Googling, three practical finance strategies, his name seems to pop up. Chris Hutchins is the host of the wildly popular podcast, All the Hacks, where he explores how to optimize every area of life, from money to travel to health, without spending a fortune. He's been featured in The New York Times, The Wall Street Journal, and CNBC, and his work in the financial independence space even landed him in the documentary Playing With Fire. But Chris' story goes deeper than hacks. He's someone who's built an incredible career and life. Head of new product strategy at Wealthfront, after they acquired his company Grove, investor at Google Ventures, co-founder of Milk acquired by Google, and creator of Laid Off Camp. Along the way, he's managed to collect over 10 million points and miles, which gives him more than enough credibility to call himself a financial optimizer. But what excites me most is not his ability to optimize. It's that Chris has reached a point where joy, curiosity, and purpose guide his daily decisions. He's not waking up every day trying to squeeze one more penny out of his portfolio.

He's living a life designed around meaning and the money serves that vision. That's a powerful shift, especially for those of us in our 40s and beyond who want to invest wisely, but also actually live well. In this episode, we'll dig into practical tools, rethinking the 9 to 5 grind, why we might have it wrong when buying health insurance, and even why prepaying for things can bring way more joy than paying as we go. Well, at least for some of us. But more than that, Chris is here as an example of what it looks like to align wealth with life and not the other way around. So grab a notebook because this conversation is full of hacks, but it's also full of perspective. And it is my absolute delight to give you this week's show with guest Chris Hutchins. And before we get into it, if you do enjoy today's conversation, the best way you can help me grow the show is by leaving a quick review on Apple Podcasts. It takes less than a minute. It helps others understand what this show is about. And it really does make a difference in reaching more people who want to build wealth and meaning. Thank you so much and I appreciate it more than you know. But I want to start where you and I have left off in a previous conversation not to get too incredibly existential and philosophical right from the get go. But you and I both produce lots of content for people to think through wealth and meaning and intentional living. So I'm wondering if you could start us off by sharing just a little bit about what that has looked like for you throughout your life. In other words, just to ask the big question, why are we doing this, Chris? What's the meaning of life or wealth to you?

Chris Hutchins (4:05)

Wealth to me started as a way to just keep up in a way. I went to a boarding school and every other kid had a credit card from their parents or unlimited money and I didn't. So it's like, how do I get pizza? I don't have the cash to buy the pizza, so I try to buy pizzas and sell slices so that I could have a little profit to eat. Wealth to me early on was money that allowed me to do the things that other people could do.

I honestly was one of the people who had no idea what I wanted to do, so I just asked around and I was like, what are really good jobs? And a lot of my high school friends were like, oh, really good jobs are investment banking and management consulting. And so I was like, well, I guess I got to go do those things. I bought those books, The Vault Guide to Investment Banking, The Vault Guide to Management Consulting, and I applied for some jobs and I got a job at a management consulting firm and investment bank and I went kind of through that path for a few years and I was like, this sucks. Like, this is life. There were parts of it I enjoyed, but it was definitely not a meritocracy, where it's like, oh, if you had a good idea or you could work a little harder, someone might view you as someone with good ideas. No, you were just doing the work that someone else didn't want to do. Straight up, I remember a night where someone said, we've got all this work to be done. Is it okay if you're here till like five in the morning? And I told my boss, I was like, well, if you have time to help, we could both go home by two. And he's like, no, not interested in chipping in. This is not a team project. This is a you're gonna pull in all nighter and I'm gonna go home and do something more fun.