An Entrepreneur Who Loves Traveling and Optimizing Money: The Story of All the Hacks
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Last month, I had the pleasure of being interviewed by my friend Mesh Lakhani, who turned that interview into an episode of his amazing podcast, Founder Stories. As I listened to it, I realized I hadn't had a chance to share my journey on all the hacks yet. So since he and the team at Lola Media did such an amazing job with that show, I wanted to air the whole story here. In

In many ways, my personal story is really the story of all the hacks. So if you're curious about my background, where the love for travel and deals came from, and how this show came to be, you'll really enjoy this episode. And please shoot me an email or a DM to let me know what you think, because this is something new for me and the show.

And if you all enjoy what you hear, check out Founder Stories' other episodes featuring one of the top NFT collectors in the world, the founder of Delight Restaurant Group, think Wendy's, Taco Bell franchises, designer and eponymous clothing brand founder, Jason Scott, and so many more. So go ahead and subscribe to Founder Stories for free on your favorite podcast app.

Also, in the spirit of sharing my personal journey, I am excited to let you all know that Amy and I welcomed our second daughter into the world this week. Everyone is healthy and it'll be an exciting and sleepless few weeks ahead of us. But I just wanted to share the news with all of you before jumping into the interview. So without further ado, please enjoy this episode of all the hacks and founder stories. A founder's journey has its highs and lows. It's not a linear path. Every founder is also a regular person.

filled with high hopes and big dreams. That middle part of their story, before they reach the top, is where we can catch them at their fullest potential. What we learn of their past gives us a glimpse into their future. This is Founder Stories.

Our founder today may sound familiar to those of you who listen to his podcast. Chris Hutchins is a money optimizer who has spent a lifetime building products. He inspired his friends and family by traveling the world on a shoestring budget. He never thought his tricks for getting the most bang for his buck would lead him to be a popular podcast host. His goal? Make your money go farther than you thought possible. This is the story of All The Hacks.

I'm Chris Hutchins. I love building products. I host a podcast about optimizing your life called All The Hacks.

Technically, I grew up in St. Louis, but we moved by the time I was four. So my memories are just really the pictures and the videos that I saw as a child. So my life growing up really was, you know, kind of outside of D.C. in the suburbs. It was kind of like your typical suburban American childhood. You know, I went to school on a yellow school bus at a playground in the backyard. It's a good life to the best. I knew it.

my parents, because they worked at home, they had computers at home and not everyone had computers at home in the late eighties, early nineties, but my parents did. And boy, like as soon as my dad got a second computer, the old computer went downstairs and I was, I was down the rabbit hole.

Yeah, dad, 28, eight modems are out. Can we please upgrade? Can we please upgrade? Dialing into BBS is goofing off on prodigy. Then AOL. Yeah. I remember when we first got an ISDN line, it was like, you know, 128 K. I'm like, wow, we're speeding along the internet now. And,

I made weird presentations for school where I would project a PowerPoint onto a TV and like record it on video and make like video presentations. So I was definitely a nerd. And then I also loved punk rock music, hardcore shows, skateboarding, BMX. Woo!

My friend down the street and I would make skate videos all the time where we'd like clip ourselves and then like we'd put other pros from other videos and it'd be like pro doing something awesome, us doing something just like not awesome, but we felt really cool about it. I always ask my parents, I was like, was I an entrepreneur from a kid? And...

They tell me some stories that I maybe forgot. And then there's definitely stories I remember. So I remember I really wanted to go to concerts for free. I've always been an optimizer trying to get the best deals. And so I was like, gosh, how do I go to these concerts? Like the Vans Warped Tour. I was like, I want to go to this, but I don't want to pay for it. So I remember making a magazine...

like a seven page magazine about punk rock. And I would like bring a copy to some local concert or a promoter and be like, Hey, I've got this magazine. Can I get into the show for free? And so I was always trying to creatively find ways to achieve outcomes that maybe weren't businesses per se, but that there was that entrepreneurial spirit in there, but never crossed my mind that this could be something I would ever do professionally. It was just like a huge passion of mine.

When I was in middle school, I had the luxury of my parents being home all the time. But I also had the challenge that they were working all the time. And so a lot of my friends maybe had one parent that didn't work or a parent that came home and were done with work at 5pm. But my parents owned companies and they were really busy.

And so I was like, I want to go to boarding school. And I begged my parents to send me to boarding school for high school because I wanted the freedom to kind of go anywhere. I was like, I can take the bus. I can take the Metro. I could go do whatever I want. I could get to my friends because they live on the campus. And I loved going to boarding school. Every time I asked them, they're like, what did you do wrong? And I'm like, no, no, it was amazing.

The high school I went to, and this was in early 2000s, I think I started in 1999. Every kid had a laptop and everything was online. You were like, if a teacher emailed you an assignment and you didn't get that email, like you're failing the assignment. That was kind of new at that age for a school to do that.

And it was super old school. Like all the computers still needed ethernet. So every single desk in every single classroom had an ethernet plug and you had to like plug your laptop in and you had to charge it because the battery only lasted like 45 minutes. We actually had a class where you could become a Microsoft certified network administrator that took that class. And we had a network. And I remember, uh,

In high school, we wanted to share games and movies that we'd all downloaded. And so we created a network that you could log into that was our network. There was the school network you could log into. And then me and these three, four guys created our own network that you could log into and share stuff. In high school...

This friend of mine sent me this email and was like, Hey, I met these guys that are selling dial-up internet service. You can sell it for them and make a lot of money. Do you want to learn about it? Sure. So I go to this meeting and they're pitching this thing that they're like, yeah, we sell dial-up internet service, but like, that's not the cool thing. The more reps you sign up under you to sell dial-up internet service, the more money you make.

This is a total pyramid scheme. So instead of walking away, I was like, gosh, what should I do? I like called up Fox 5 in D.C. and was like, I need to talk to the investigative reports team. I've got something for you. And we ended up bringing a like an undercover camera. I had like a camera on a button on my shirt and we hit another camera in a room and I had a fake bra.

brother or cousin. I can't remember. I emailed them. I was like, Hey, I don't know how I feel about the pitch, but my brother's obsessed. You guys got to come talk to him. And we did like an undercover sting operation where we exposed the pyramid scheme and all that kind of stuff. And it ultimately that company never existed. I guess a theme in my life was if something can't be done, let's just try it anyways. Boarding school had really prepared me to not...

have to deal with all of the stress that comes from living away for the first time when you go to college, figuring out what that's like. And so when I got to college, I was like, let's do all the things.

And so I remember a lot of the kids I went to high school with were always posting online. And this is like early days of Facebook where like the only thing you do is post what you're doing. And so people are like, oh, I'm at this concert. And I was like, how are you going to this concert? Like, oh, our school put on a concert. And I was like, what do you mean your school? My school doesn't put on concerts. And if we do, there's certainly nothing anyone wants to go to or they're not that exciting.

So I was like, hmm, I wonder how you can do that. And I was in student body government at the time. I was like, oh, you know what? Anyone can rent the stadium, like a basketball stadium at school. Anyone can get permits to reserve the parking lots. So I was like, oh, what if I just put on a concert? I talked to a friend of mine who was like way more into music than I was, at least more mainstream music. Dude, what's the band that we should do a concert for? And he's like, I got this band and they're going to be huge. They're called The Fray.

I have no idea what that means. And he's like, they're really good. I'm going to go on a limb and trust you because I have no idea what this band is. But thanks to my trusty friend, Kevin, that we booked the fray. And then we went to the school and we're like, we need to rent the stadium. Can you guys sell tickets for us? So we ended up selling tickets. We ended up putting on this concert, but like we didn't hire a production company.

We did for lights and sound, but not for making the whole event work. VIP backstage passes were things that I printed on a printer in my room and I bought a laminator to laminate them. And when we had to make a green room, we literally took couches from our apartment. We went to Walmart to buy the stuff people asked for in their riders. It was the most amateur experience you could imagine. But...

It all went off. And I think we probably made like five grand, which in college was like the most amazing amount of money ever split between three or four people. And it's a theme in my life that I guess sometimes gets you into trouble, but oftentimes leads to exciting things.

I've asked in almost every company I've worked at, let's go meet with the CEO. Let's go meet with the person running this team. And I've been told sometimes, oh, you can't do that. I'm like, why not? I'm just going to try. So in college, I was like, I'm just going to go schedule a meeting with the dean of the business school. And I didn't know until later that he's on a bunch of boards, knows a lot of companies. The deans of colleges and the people who run the school, they're pretty connected.

So I was just like, "I'm gonna go meet with him." It wasn't a thing that most people were doing, but it turned out to be the only reason I got a job after I graduated. That might be actually one of the best college indirect advice I've ever heard. Try to make a relationship with the dean, introduce yourself when you get there. That is the first... I'm 37 years old. That's the first time I'm like, "Oh, that would have been actually smart. I should have done that." I never really knew what I was going to do after college.

What ultimately happened was I went home over Thanksgiving and I connected with a bunch of friends that I went to middle school and high school with, and they all had jobs. And I was like, what do you mean you have a job? And they're like, this is when all the companies hire. Like if you want a job at top companies, it's gone. And so I went back to school after Thanksgiving, before Christmas, and I went to the dean and I said, Hey, I need a job in management consulting or investment banking. Can you help me?

He came back. He said, I know a guy who works at one management consulting firm. And I sit on the board of this company. And there's another guy on the board that works at an investment bank. He's like, I'm going to introduce you to two of them. Sure enough, I hear from the management consulting firm, yeah, you missed the boat. The cycle to get a job after graduation is over. But if you want to interview, you can interview for the next cycle. And I was like, great, let's do it. Bring me in. So I came in, I interviewed there. And then the investment bank said...

We don't hire people out of college, but we have an internship that you could do. And if it works out, maybe it turns into a job, but probably not. Fortunately, at the end of the internship, they offered me to stay on. But it wasn't stay on, you're now on the same ranks as all of the associates. It was like stay on as a full-time intern kind of thing. But instead of having a class of 20, where I had 19 other people to help out with all the work they wanted the interns to do...

It was just me. My breaking point was a week where I didn't see my wife awake. At the time, girlfriend, I didn't see her awake for five days straight.

And I went to management consulting. I guess I thought it would be a lot different, but it was pretty similar. Maybe swapping out Excel for PowerPoint. In management consulting, it's all about slides. In investment banking, it's all about spreadsheets. But my experience in management consulting was one where I really understood what an entrepreneurial spirit is and how it can be crushed.

It's a job that provides you a ton of access to interesting problems and really smart people, but it's not a place in most firms or the firm I was at where if you have an idea that could be really interesting at a more senior level that you could do that. Science has shown that being charitable can actually have a huge impact on your happiness, which is why I'm excited to be partnering with Daffy today.

They're a not-for-profit community built around a new modern way to give, and they have a mission I think we can all get behind, helping people be more generous more often. Amy and I use Daffy for all of our giving because they offer an account that makes it easy to put money aside for charity. You can make a one-time contribution, or you can set a little aside each week or month, and all your contributions are tax-deductible.

Except you don't actually have to know exactly where you want to give the money right away. In fact, you can make your tax-deductible contribution now and invest that money into stocks or even crypto so it can grow tax-free and let you have more impact in the future. Then, whenever you're ready, you can give to any of more than 1.5 million charities, schools, or faith-based organizations in a matter of seconds.

So head on over to allthehacks.com slash daffy if you want to start giving today. And for a limited time, if you visit that link, you can get a free $25 to give to the charity of your choice. Again, that's allthehacks.com slash D-A-F-F-Y.

So I am quite comfortable right now, which is actually true almost every day. And that's thanks to Viore. And I'm excited to be partnering with them for this episode. They make performance apparel that's incredibly versatile. Everything is designed to work out in, but it doesn't look or feel like it at all. And it's so freaking comfortable. You will want to wear it all the time. Seriously, I am pretty sure it's more comfortable than whatever you're wearing right now, unless you're wearing Viore, in which case you already know what I mean.

And it's not just for men. My wife is as obsessed with Viore as I am. My favorite is the Sunday Performance Joggers. I think I have three pairs, and they are probably the most comfortable pants I've ever owned. Their products can be used for just about any activity, whether it's running, training, or yoga. They're also great for lounging, running around town, or their MetaPants can even work for a night out.

Honestly, I think Viore is an investment in your happiness. And for all the Hacks listeners, they are offering 20% off your first purchase as well as free shipping and returns on U.S. orders over $75.

So you should definitely check them out at allthehacks.com slash Viore or in the link in the show notes. Again, go to allthehacks.com slash V-U-O-R-I and get yourself some of the most comfortable and versatile clothing on the planet. Then one weekend, I heard about an event called Startup Weekend that a guy named Andrew Hyde started and everything for the rest of my life changed in like a flash.

And that was in October 2007. So despite living in New York City at the time, I knew the financial crisis was happening, but it didn't really hit me until a year later. But...

Startup Weekend was crazy. I drove up to Boston. This event had happened in Boulder. I don't even know how I heard about it. And I drove up to Boston. I didn't even have a place to stay. I was like, I'll sleep on the couch. It doesn't matter. This sounds cool. And the idea was get together engineers, designers, product people, just anyone. And in the weekend, let's start some companies. So I joined this team and we built a product called Desk Happy.

And it was a Windows app that every some odd number of hours would remind you to stretch or stand up or kind of do anything. It reminds me of like the Apple Watch pause to breathe kind of thing. But back in 2007 and it didn't go anywhere. Like 250 people used it. And I'm fairly certain that like they were all the friends and family of the people that were in the room.

But I realized, wow, in 48 hours, we built a company that like makes a product online that people could buy if it were actually good. And, you know, obviously we didn't spend that much time on it. This is crazy. This is a job. What I'm doing right now, helping build a product is a thing I could do for a living. I was like,

what am I doing with management consulting? Andrew was like, Oh, I'm doing another one in San Francisco. I was like, I'll be there. And while we were there, I ended up meeting some really fascinating people. And I was like, I got to do this. I came home and I was like, Amy, you don't even love living in New York. How would you feel about moving to San Francisco? I was like,

So Amy, my wife, who is incredible and has supported me through, I don't know, like 10 different jobs and experiences. And we met sophomore year in college. Hello, I'm Amy. We didn't get married for a while. I think in our minds, it was like, we just have so much going on. We don't know where we're going to live.

we were kind of very practical about it saying like, look, we need to make sure that we're living in a place that we both want to live for a long time. She grew up in Colorado. I grew up in DC in New York. We were like, we don't want to live in New York forever. And San Francisco ultimately ended up being that she kind of felt like New York wasn't the place for the longterm. And the company I worked for only had offices in Chicago, New York, Boston, San Francisco, and LA. We came up with reasons that the other cities didn't work. And it was,

She didn't love her job at the time. So we were like, great, let's move. And at least I'll be able to keep my job. And then we were like, okay, we should probably find an apartment. And then like a week later, I get this message to like come to the office and have a meeting with a person I've never met before who ultimately laid me off. This was October, 2008 by now, you know, it had been a year of startup weekends, trying to figure out how to move, moving out. Like it wasn't, it didn't all happen in a week.

But we were in the middle of the financial crisis. This was a major situation. I was like, look, I moved to San Francisco to go work in tech. I didn't move here to work in management consulting forever. So I was ready to leave. We're trying to figure out what to do. I have no job. No one's going to hire you between Thanksgiving and Christmas. Companies are closed. Also, no one's going to hire you because the entire economy is crashing. It was definitely a blessing in disguise because I ended up getting to find all the crazy cool stuff that ended up following. But...

Well, I was kind of pissed. Like, just let me go right in the middle of the holidays. And one of the things that I ended up doing was going to South by Southwest. I went to this event at South by Southwest called Bar Camp. The idea was you create this conference and people just make up topics on the fly. They were kind of mostly technology related. People are like creating events, but there's no organizer. Flashback to the days that we put on a concert in college on our own. It was like we put on a conference on your own. You just say...

when whoever shows up writes on a sticky pad, this is a topic I could lead a discussion about or teach people about. You create a schedule on the fly of what the day is. And it occurred to me that there are so many people that are unemployed right now and I'm one of them.

Options are find a job, start a company, start freelancing. And I knew nothing about any of those things. So what if we just put on an event? Let's call it Laid Off Camp. And next thing you know, I put on an event with the help of a lot of other people, with hundreds of people showing up, with the media from all over the country. Being laid off can feel pretty lonely, sitting at home, searching the internet for jobs, worrying about the future. It's called Laid Off Camp.

Maybe it's the idea of camp, even if it is for laid off people. It's taking place at a club in downtown San Francisco. So there's white leather couches and music. It just like really captured the spirit of where the economy was in a way that I never anticipated. And it was totally open source. So I actually created a website that was a wiki. I said, if you live in another city and want to do this.

Here's the email I sent to sponsors. Here's the schedule. Here's how I organized it. And there ended up being 20 of them around the country. And it was very temporal. The economy kind of recovered. People got jobs and it kind of just withered away and laid off campus no more, which is totally fine. But...

It was an awesome chance to meet lots of people. And it was a huge opportunity to kind of grow in a city that I had only been in for a very short period of time, but very quickly wanted to try to immerse myself in. So after that, you would think the story would most logically be, I met these companies, I started working for them and I had all these fun jobs, but it's a little different.

So a company said, "Hey, you put this event on. We want to put on an event to engage our users and our clients. Could you help us put on a series of events?" And I was like, "Cool." So I worked with this company outright. Another company came to me and said, "Hey, we're trying to do a..." I think it was like a Series C fundraise, which now is probably like a Series F. One of their investors said, "Hey, can you put together some financials of what's going on in your business?" And they had no experience doing that. And they were like, "Hey, you used to work at an investment bank. Can you help us?" So I was like working with this company called

called UserVoice to put together their financials and their projections in their pitch deck for their fundraising. I didn't love freelance work because it was kind of very much, you don't have the end ownership in the project. But at the time, in the wake of the financial crisis and not knowing where I would work, it was great to have an income. It all comes to an end. However, any freelance gig usually has an ending. And so I was, I guess, unfortunate and fortunate that they were all coming to an end at the same time.

So normally you try to stagger these things out. So if you have three clients and you go to two, you can get a third. Well, I went from three to zero in like a month, but I knew it was coming. And so a month out, I asked my wife, I say, Hey,

if I'm going to have no job for a month, should we take a trip? I put a lot of the expenses from laid off camp on my credit card. I'd become like an optimizer. So I'd signed up for different cards to get signup bonuses. So we had some miles. I was like, let's take a trip. And my wife said, let's do it. So we bought a map, we put it on the wall and we bought like push pins. And we were like, let's put some push pins in the countries that we're excited to visit. There were so many pins. We were like, how are we ever going to do this? Like cluster them together. We're like, Oh, if we want to go to these two countries, we're like,

that's a two week trip. We're going to go to these two countries. That's a two week trip. As I was doing all this research on which countries to go to, I found people that were like effectively, like they quit their job. They, whether they did a gap year, they became nomads. Like they went on these extended trips. And I was like, that's interesting. And if you look at any trip that you've been on, the main cost of a trip is usually getting there. The flights are the big cost.

The lodging would be the second biggest. We realized, wow, if we could stay with interesting people around the world and we could travel slowly, meaning like take a bus between two countries for a dollar instead of a flight for $300, the trip wouldn't actually cost that much more. And we could sublet our apartment. And like all of a sudden we realized...

We're taking a long trip. And so we decided, let's quit. Let's take a trip. So we ended up flying one way to South Africa. And over the course of eight months, we trekked up Africa through the Middle East and through Southeast Asia and India. We probably spent, I think, $7,000 each for an eight-month trip around the world. If you do the math and you take $7,000 and you divide it by eight months... We're talking like $30 a day.

So that's food, that's activities, that's transportation. So we were finding crazy ways to take a 52-hour train ride from Zambia to Tanzania. I've always been a person that's looking for the best deal, and I try to go back to figure out where that started. My dad definitely played the points and miles game, and we would take trips as a kid in business class using his miles to Europe. So I always knew that existed.

I was always trying to figure out like, what's a way to get what I want without having to spend money. And in college that was opening up credit cards for bonuses to be able to take trips for free. And on this trip around the world is where it kind of, it was just like a daily occurrence because we had no money. We had money to go on this trip, but it

If we spent it all, we had to go home early. We knew we had enough miles to get a one-way ticket back home from anywhere in the world. So we knew at some point we would go home, but the more optimal we could be, the longer we could go. And so we were couch surfing almost the whole trip. We found people on a Lonely Planet forum on the internet who also wanted to travel around Namibia and Botswana. And we like rented a car.

We bought a used tent and some sleeping bags and the four of us, my still not yet wife and girlfriend and two guys from Sweden, like shared a three person tent and rented a Toyota Yaris and like drove around Southern Africa and a few countries. And so we were always trying to be super optimal. I came back and everyone's like, how did you do that?

Every person you talk to when you say, "I took eight months, I went around the world, I saw these amazing things, and I spent $7,000," they're like, "I want to do that." After that trip, it was just like my identity.

I remember one of the things I did right as we were leaving, submissions were due to speak at South by Southwest. And I was like, gosh, you know, the next step for me is like to build a network, you know, in a more elevated sense in this tech community. Because I knew whenever I came back, I wanted to work in tech. I wanted to work at a startup. So I was like, man, if I could speak at South by Southwest, that'd be really cool. So I submitted this talk about what it's like to be unemployed and start things. It was called like fun employment in the wake of the crisis or something like that.

So I was in Turkey and we were like literally sitting in a guest house carved into the side of the mountains of Cappadocia, but they had internet and I logged on. It was like, your talk was approved. And I was like, what?

really? I thought it was a big long shot, but I was like, I'm going to be a speaker at South by Southwest. This is like, this is next level. We have four or five months left, but March is when it ends. And we were like, the end is Singapore, right? Like you get to Singapore. So we were like, great. I'm going to book a flight from Singapore to Austin and I'm gonna go to South by Southwest straight from the trip.

And I now have this new mission, which is I am going to work for whatever I can find to be the hottest startup there is. Like I want to work for a name brand, amazing startup. That is my mission. South by Southwest is my opportunity to find it. All these founders and investors are here. This is like what my new life is.

I was convinced that I found it. I found this company called Simple Geo right after the iPhone 3GS came out. So we all had mobile phones and they had GPS, but nobody really knew what to do with it. And their whole idea was we're going to build software that enables developers to use location in their products. I had met casually one of the founders. I wasn't sure how to do this.

So I made this presentation that was all about the industry and what's happening and the opportunities. And I had one person I knew well enough who was an investor in the company. And I was like, can you send this to the founders and let them know? I would love to talk to them. At the time, I thought this is a long shot. I now realized that if a person is that excited to work for you, just hire them. So I worked full time at this company in business development. But ultimately, the startup didn't work.

Around the same time, I had connected with a couple people who had started and worked early at a company called Dig, which was like Reddit before Reddit. They were starting a new company. It was so early. This is pre-starting. And they were like, Hey, do you want to come join our founding team? And we're going to build this incubator to build products. And I was like, Gosh, yeah, of course.

By the time I was joining Milk, I felt like I had a good sense of the community and the products and the companies in that aspect. But I had no clue really how to build a consumer product. Simplegeo was building an API dev product, but they were not building something for consumers. So now is this whole new world of, "Well, I got to do customer research. I've got to figure out how things work." And so Milk was my chance to learn how to build consumer products.

So I came in and I don't even know what my job was at the time. I was in charge of HR, payroll, BD, partnerships. I was learning everything. I didn't know how to set a payroll. I didn't know how to get benefits for a company. I didn't know how to do any of this, but I was like, I'm going to learn and I'm going to ask everyone I can for advice.

And throughout that experience, I was like, wow, I feel like I accelerated my ability to hold my own in the tech community and found a home. At least I think I found a home of building products was really cool. But we were trying to figure out how to make the model work. We built a product that was pretty cool. And we were in this crossroads of...

Do we try something new? We're an incubator. Do we double down on the thing we built, which we didn't have enough conviction in to do? Or do we take all the skills of what we learned and apply them at a bigger company? We had the opportunity to do that at Google. And so we sold the company to Google. Going through that negotiation, I was frantically trying to make sure all the pieces were in the right place and organizing all the diligence information and...

You know, when we landed at Google, and this is so silly, was that finally, people who didn't work in tech had some sense of what I do. Like, I'm working at this startup that you've never heard of. Okay. You know, you go to family reunions. People don't believe that you even have a job. They're like, what are you doing? And now I'm like, I work at Google. And they're like, I know Google. I search for things with it. Like, it relates. So I go to Google. And through the interview, they were like, you are a product manager.

I didn't know where I would get placed through these interviews. And so I was like, "You're a product manager." So I tried my hand at product. It was a frustrating experience because I was working on Google+, which was a project that at the time had about 100 product managers and 1000 total people working on it. And my running joke has always been that at any given point in time, there were more people working on Google+ than using it.

We were trying to figure out if there was a better place at Google that we could spend our time. And I had raised $250,000 for milk from Google Ventures. So I went to the team that we raised money from and I said, "Hey, you guys all work at Google. You probably know this org better than we do. We've only been here a few months. Where should we work?" And then they came back and they're like, "Actually,

You and Kevin have very distinct skill sets. Kevin's been a very successful seed investor and you're like at every event in the mix with everyone. And like, that's not something we'd really been doing. Like we'd been really focused on a different style of investing. Why don't you come and do seed investing here? We moved over to Google Ventures and for the first time in my life, I had a job that lasted for more than one year.

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I just want to thank you quick for listening to and supporting the show. Your support is what keeps this show going to get all of the URLs, codes, deals, and discounts from our partners. You can go to all the hacks.com slash deals. So please consider supporting those who support us. Now I'm about to go into venture capital, right? I'm about to pick startups and I'm reflecting on my ability to do that.

having joined a startup that didn't work, joined another startup that didn't work, but fortunately got acquired. Meanwhile, if we rewind to coming back from the trip around the world, the talk I gave at South by was with a friend of mine named Matt Van Horn, who at the time also worked at Dig.

He had a friend that I think was friend from college or maybe from childhood that was starting this company called Zimride. They basically replaced that message board that we had in college, if you're old enough to remember, where you were like, Hey, for Thanksgiving, I'm driving here. Does anyone want to get a ride? We didn't have some cool app to do it with. And so they were long distance ride sharing. It was replacing going on Craigslist to mean like, who wants to drive to LA this weekend and split gas? Yeah.

And for some reason, I was like, I'm not that interested in this company. But they were also hiring people in sales. And so I told my wife, I was like, hey, you should meet this company. And we just got back from this trip. She didn't have a job. She ended up loving the team and joining as one of the first... I think she was number five on the team at Zimride. And the irony in all this is my mission coming back from this trip was to pick the hottest startup in Silicon Valley.

And I met the guys at Zimride. I was like, "This is not the hottest startup. I'm going for Sybilgeo. Sybilgeo is the one." So for those who don't know, Zimride became Lyft. My wife ended up working at Lyft for 10 years, getting arguably an even more advanced and accelerated learning experience than I did watching a company go from 5 people to a public company. And then now here I am going into venture capital where my job is to pick which company will be successful.

And yeah, I'm working at Google Ventures. And I was there for three years. Boy, it was the most fascinating thing in the world to be able to sit in on these pitches of late stage companies. Here are the questions that smart people that I worked with were asking. And I thought, wow,

this is finally my opportunity to work at a company for more than one year. This kind of all ties into money in a weird way. I'm still wildly frugal at this point in my life and now as well. But all of that, I think, stems from the fact that I keep having jobs that I never truly knew that I could do forever. One year into venture capital, I'm really enjoying it. Maybe I can spend money now because I know that there will be money coming in the future. My worry my whole life was I could never find a thing I love doing. And if I couldn't,

I didn't want to do something I didn't love, so I wouldn't have money. So I was like aggressively pursuing financial independence, trying to save every dollar I could because I didn't know that there was a thing I could do that made me happy that generated an income. But two or three years in, I think, gosh, this is fun.

But I just don't know if this is for me forever. It wasn't that venture capital wasn't fun, right? It wasn't learning. But I think I had this thing inside me that I don't anymore think is true. But at the time, I thought, how can I go invest and help these companies if I've never actually done it myself? Like I've never been the CEO of a company. I've never seen it through. Inside, I was like, I can't do this forever. I can't move out of seed and do later stage investing if I haven't been there and done that.

A problem that I noticed everyone having, and they're coming to me, they know that I'm obsessed with personal finance. So everyone's asked me what to do with money. They're like, hey, we're getting married. What do we do? Do we combine our finances? Hey, what do we do with our savings? We actually have money. Hey, we're thinking about buying a house. Should we do that? How much house can we afford? And I'm like, people don't know what to do with their money. And the more I learned, nobody knows what to do with their money. So I was trying to figure out what could solve that problem.

And I heard about this practice that exists called financial planning, which was different from managing your investments. It's about creating this comprehensive plan. And I was like, wow, this is interesting. I wonder...

If that process of going through a financial planning process would solve all these problems, these people keep coming to me with about money. Everyone should have a financial plan. Like everyone's stressed out with money. Everyone should have a financial plan. How do we solve that? And I connected with the friend from middle school who we built dungeon games on our computers. We've been talking about this. And every time someone had questions, he was my like, okay, let me think about that and get back to you.

So he decided to move to California. He lived in our spare bedroom and we were like, let's start this company if it works. And if we can raise a series a, he's like, I'll talk to my wife and we'll move to California. But if we can't, I'll just go back.

And so ultimately, we left. I told Google Ventures, "I got to work on this more." Thankfully, my wife was now at a much later stage Lyft, had a much more stable income and could support effectively going all in on "Let's do a startup. Let's found it. Let's be the CEO. Let's be the one in charge."

Step one, we had to see if the product works. So we just made a product. We created a registered investment advisor. We went through the regulatory filings. We started helping people to prove that this worked and collecting enough data that ultimately we were able to raise money. And so we pitched investors. The way seed investing often worked, at least at the time, was that there were a lot of funds that didn't want to leave. So people were like, I'm kind of interested, but I'll get back to you. And like, all it took was a lead. And if you didn't have a lead, everything fell apart.

So we dug in. I remember my co-founder and I sitting at my dining room table where we were working saying like, gosh, if this doesn't work by next week, I think we call wrap it up, call it, call it done. And then like an hour later, I finally get the call from first round there. We want to lead.

And so fast forward, a fun process that now that you have a lead and it's a good lead, everyone else is like, oh yeah, I'm totally in. I know I did. I said I wasn't sure, but now I'm in. And so now we were like, oh, how do we put this round together? How much is it? How do we fit everyone in? It went down a totally different path. Co-founder decided, okay, we're going to move out. His wife, he and his wife moved out. They still live out here in Palo Alto. He's now working at Stanford.

And so we have a round and we're like, "We're off to the race. We got to hire people. We got to get an office." And we scaled up a team. We continued building a product. We launched. We had a waitlist that was longer than we could handle. But in raw numbers was hundreds of people. And we had proven hundreds of people were willing to pay us. We had a paid waitlist to use our product. But when we finally had the capacity to take people off the waitlist, they all said,

"I'm not ready yet." And we're like, "Oh, do you want your money back?" And they're like, "No, no, no. Keep the $50. I want to do it. I just want to do it right now." The lesson we learned brutally over the next year was that everyone wants financial planning, but nobody wants to do it right now. To scale customer acquisition beyond that group of 1000 people that really wanted it now, there was latent demand of people like, "I just want this." And at a lower price, it's amazing. We just couldn't scale it. $4 million still in the bank, we realized like,

Human-powered financial planning is not a product that you can lead with. If you want to do it at scale, it has to be a complementary product to something that has an urgency of using now. And I was also thinking at the time with my co-founder that maybe we don't need humans. Maybe you could implement all this in software. We still would have the problem that people aren't ready for it now, but we are starting to come to the conclusion that maybe that would be possible. We weren't sure.

And around the same time, I had a conversation with Andy Ratcliffe, who was running Wealthfront. And he said, look, we have this vision for self-driving money. We want to automate all of the financial planning and everything. We'd love people to come help work on that. And we're like, this is a great opportunity. And I've spent the last two and a half years working on all kinds of other personal finance products at Wealthfront, trying to ultimately solve the same problem, which is to help people make growing their wealth easier.

Meanwhile, while all this is happening, I still haven't convinced myself that I found a job I can work at forever. Because the startup was not working. Now I'm at Wealthfront. And so I still have this thing in my core, which is...

You still need to keep optimizing to save money. But I still want to do crazy fun stuff. And so I'm constantly exploring ways to optimize every aspect of my life. And that just dominates every conversation I'm having. And it's just become my passion. What I spend my time on, on the nights, on the weekends, what I'm sharing with friends and what I've become known for. I have friends that are now like, you're my travel agent. And I actually got my travel agent license so that I could be actually a travel agent and book trips for them.

The crazy thing that happened is, as we all know, there's the pandemic. And in some ways, I think people during the pandemic had more time to sit at home and do things like think about their finances because they weren't out doing other things. And I kept getting all these questions. And I was like, man, there's all these people asking me questions. And it's so unscalable to have one-off conversations. Before, it would be like a dinner party with six people. It felt a little better.

And so Kevin from Milk, my old co-founder, ended up saying, you got to start a podcast. And I thought, yeah, let's do it. I actually joined him on his show to talk about money hacks. At one point, he said, hey, tell me about your new podcast. And I was like, well, I haven't started it yet. And he's like, yeah, we'll cut this part out. You just need to record an answer to your new podcast and send it to me by Friday.

And so I went home and I was like, "Okay, what's this podcast about? What's the theme? What's the trailer? What's the music?" And put it all together. And it's just blown past my wildest imagination. Because it turns out there are a lot of people out there that want to optimize their life. They want to do it while spending less money. They want to travel around the world and they want to do it in first class if possible. So what are all the hacks to figure out ways to do that? To save money when you're shopping online and the holidays?

to invest smarter, to use crypto to your advantage. All of this stuff is stuff we cover in the podcast. And now I spend a lot of my time, mostly on my nights and weekends, just digging into all the hacks, talking to the most interesting people I can. And that's my avenue for sharing all of these things with the world. We also start a newsletter. So if you don't like to listen... Well, I guess if you don't like to listen, I don't know why you're here right now. But we have a newsletter that complements it pretty well.

Now, can I turn it into a real business that finally fuels the burning desire to have something sustainable that I love? Maybe, you know, I'm finally feeling like maybe I can start spending a little money, but keep in mind for me, that's like, I can finally order an extra appetizer. You know, spending a little bit more money for me is not as crazy as it is for some people, but I'm working on it. And I did a great episode with Ramit Sethi about this, where he's like, look, you got to learn how to live your own rich life. Everyone has a different version of it. You

You can find your version and you can create rules that allow you to have a little bit better relationship with money. You know, we talked a lot about my girlfriend, my girlfriend, my girlfriend, right? And the fun story to throw back to our wedding was I remember when we were getting married, I had seen a video from...

Someone I knew but didn't know that well who had a lot of money's wedding and they posted online. I was like, wow, that was a really impressive video. Like, gosh, if you could capture your wedding in that way, it would be wonderful. So at the end of the video, there's like a little tag for who made it. I reach out and I'm like, I would love to do a wedding video. I should have known that when they don't post their prices online, it means they're probably a lot. So ultimately I'm like, oh, wow.

It was over $10,000 for someone to make a wedding video, but I really wanted to do it. I got to talking to this woman who's now become a friend of mine. She was living in LA, but she was from Colorado. Amy, my wife was from Colorado and we went to school there. We were just having good fun conversations. And it came up that we were going on our honeymoon to the Seychelles. I thought for our honeymoon, let's go to the wildest, craziest place we could go. And let's of course do it on points. You know, we ended up taking this honeymoon that cost $1,000.

Just the flights alone were like $20,000. Probably the hotels were probably another $10,000, $15,000. We did all for free. You know, if you use a credit card that earns two points and those points are worth two cents, then you're effectively getting 4% cash back. We were getting like a crazy value from being able to fly first class around the world. We ended up doing it in like some of the best airlines with like private suites and everything. But it was all points. I was telling...

this woman, Julie, who ran this production company about this trip we were taking. And she was like, you're literally describing my dream vacation. And I was like, what if we just send you on that vacation also? And you do the wedding for free.

And she was like, I got to talk to my husband. And she came back. She was like, we're in Delta had this crazy promotion where if you send people miles, they would double them to charge money, to send people points, but not nearly enough that it mattered if they were going to double it. So we had all the points ready to book this flight and,

I transferred them from my account to my wife's account. And instantly we had twice as many. For $1,000, we doubled the Delta miles that we needed to go on this trip. And I was like, boom, I just got our wedding video. Like I had this extra 240,000 points sitting here that we then used to send them. And they had an amazing time.

And the trip probably would have cost them $20,000. So for them, they got a trip worth more than the wedding video. For me, I got a wedding video that we'll have for the rest of our lives for like the thousand dollars it costs to double my Delta miles. Those kinds of optimizations, those kinds of ways to enrich your life and upgrade your life are exactly what I like live and thrive for and love sharing every week on Wednesdays at 2 a.m.

I just want to jump in and say thank you so much for listening this week. If you enjoyed hearing my story, or honestly, even if you didn't, please let me know. DM me or email me, chris at allthehacks.com. We'll be back with another interview next week. And if you enjoyed this style of interview, you can check out more from Founder Stories. See you next week.