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00:01:34.640 | Hello, and welcome to another episode of All The Hacks, a show about upgrading
00:01:41.600 | your life, money, and travel.
00:01:43.360 | I'm your host, Chris Hutchins, and I'm excited you're here today because we're
00:01:46.840 | going to do something different.
00:01:47.920 | Last month, I had the pleasure of being interviewed by my friend, Mesh Lakhani,
00:01:52.760 | who turned that interview into an episode of his amazing podcast, Founder Stories.
00:01:57.280 | As I listened to it, I realized I hadn't had a chance to share my
00:02:01.000 | journey on All The Hacks yet.
00:02:02.600 | So since he and the team at Lola Media did such an amazing job with that show, I
00:02:07.340 | wanted to air the whole story here.
00:02:09.280 | In many ways, my personal story is really the story of All The Hacks.
00:02:13.200 | So if you're curious about my background, where the love for travel and deals came
00:02:17.060 | from, and how this show came to be, you'll really enjoy this episode.
00:02:21.040 | And please shoot me an email or a DM to let me know what you think, because this
00:02:25.280 | is something new for me and the show.
00:02:27.160 | And if you all enjoy what you hear, check out Founder Stories' other episodes
00:02:31.360 | featuring one of the top NFT collectors in the world, the founder of Delight
00:02:35.300 | Restaurant Group, think Wendy's, Taco Bell franchises, designer and eponymous
00:02:39.720 | clothing brand founder, Jason Scott, and so many more.
00:02:43.080 | So go ahead and subscribe to Founder Stories for free on your favorite podcast
00:02:46.960 | app. Also, in the spirit of sharing my personal journey, I am excited to let you
00:02:51.800 | all know that Amy and I welcomed our second daughter into the world this week.
00:02:55.280 | Everyone is healthy, and it'll be an exciting and sleepless few weeks ahead of
00:02:59.120 | us. But I just wanted to share the news with all of you before jumping into the
00:03:02.600 | interview. So without further ado, please enjoy this episode of All The Hacks and
00:03:07.280 | Founder Stories.
00:03:08.240 | A founder's journey has its highs and lows.
00:03:12.000 | It's not a linear path.
00:03:14.360 | Every founder is also a regular person filled with high hopes and big dreams.
00:03:19.920 | That middle part of their story, before they reach the top, is where we can catch
00:03:25.240 | them at their fullest potential.
00:03:26.800 | What we learn of their past gives us a glimpse into their future.
00:03:31.160 | This is Founder Stories.
00:03:33.960 | Our founder today may sound familiar to those of you who listen to his podcast.
00:03:41.080 | Chris Hutchins is a money optimizer who has spent a lifetime building products.
00:03:46.080 | He inspired his friends and family by traveling the world on a shoestring
00:03:50.280 | budget. He never thought his tricks for getting the most bang for his buck would
00:03:54.440 | lead him to be a popular podcast host.
00:03:56.800 | His goal? Make your money go farther than you thought possible.
00:04:00.840 | This is the story of All The Hacks.
00:04:03.880 | I'm Chris Hutchins. I love building products.
00:04:08.000 | I host a podcast about optimizing your life called All The Hacks.
00:04:11.760 | Technically, I grew up in St.
00:04:13.320 | Louis, but we moved by the time I was four.
00:04:15.920 | So my memories are just really the pictures and the videos that I saw as a child.
00:04:20.200 | So my life growing up really was, you know, kind of outside of D.C.
00:04:23.960 | in the suburbs. It was kind of like your typical suburban American childhood.
00:04:28.120 | You know, I went to school on a yellow school bus.
00:04:30.480 | We had a playground in the backyard.
00:04:32.560 | It's been good life to the best.
00:04:33.880 | I knew it. My parents, because they worked at home, they had computers at home and
00:04:37.520 | not everyone had computers at home in the late 80s, early 90s.
00:04:41.320 | But my parents did. And boy, like as soon as my dad got a second computer,
00:04:45.200 | the old computer went downstairs and I was I was down the rabbit hole.
00:04:48.440 | Yeah, dad, 28.8 modems are out.
00:04:51.680 | Can we please upgrade? Can we please upgrade?
00:04:53.640 | Dialing into BBS's, goofing off on Prodigy, then AOL.
00:04:58.560 | Yeah, I remember when we first got an ISDN line, it was like, you know, 128k.
00:05:02.560 | I was like, wow, we're speeding along the Internet now.
00:05:05.800 | And I made weird presentations for school where I would project a PowerPoint
00:05:10.800 | onto a TV and like record it on video and make like video presentations.
00:05:14.400 | So I was definitely a nerd.
00:05:15.800 | And then I also loved punk rock music, hardcore shows, skateboarding, BMX.
00:05:20.840 | My friend down the street and I would make skate videos all the time
00:05:25.360 | where we'd like clip ourselves and then like we put other pros from other videos
00:05:29.480 | and it'd be like pro doing something awesome, us doing something just like not
00:05:33.240 | awesome, but we felt really cool about it.
00:05:36.040 | I always ask my parents, I was like, was I an entrepreneur from a kid?
00:05:38.840 | And they tell me some stories that, you know, I maybe forgot.
00:05:42.560 | And then there's definitely stories I remember.
00:05:44.040 | So I remember I really wanted to go to concerts for free.
00:05:47.080 | I've kind of always been an optimizer trying to get the best deals.
00:05:49.760 | And so I was like, gosh, how do I go to these concerts?
00:05:51.760 | Like the Vans Warped Tour.
00:05:53.200 | Like I was like, I want to go to this, but I want to pay for it.
00:05:55.560 | So I remember making like a magazine, like a seven page magazine about punk rock.
00:06:00.720 | And I would like bring a copy to some local concert or a promoter and be like,
00:06:05.960 | Hey, I've got this magazine.
00:06:07.200 | Can I get into the show for free?
00:06:08.800 | And so I was always trying to creatively find ways to achieve outcomes that maybe
00:06:14.800 | weren't businesses per se, but that there was that entrepreneurial spirit in there.
00:06:19.160 | But it never crossed my mind that this could be something I would
00:06:21.280 | ever do professionally.
00:06:22.720 | It was just like a huge passion of mine.
00:06:24.480 | When I was in middle school, I had the luxury of my parents being home all the
00:06:29.040 | time, but I also had the challenge that they were working all the time.
00:06:31.760 | And so a lot of my friends maybe had one parent that didn't work or a parent that
00:06:35.520 | came home and were done with work at 5pm.
00:06:37.800 | But my parents owned companies and they were really busy.
00:06:41.360 | And so I was like, I want to go to boarding school.
00:06:44.040 | And I begged my parents to send me to boarding school for high school because I
00:06:48.120 | wanted the freedom to kind of go anywhere.
00:06:50.280 | I was like, I can take the bus.
00:06:51.320 | I can take the Metro.
00:06:52.440 | I can go do whatever I want.
00:06:53.920 | I could get to my friends because they live on the campus.
00:06:56.800 | I loved going to boarding school.
00:06:58.800 | Every time I asked them, they're like, what did you do wrong?
00:07:00.720 | And I'm like, no, no, it was amazing.
00:07:02.120 | The high school I went to, and this was in early 2000s, I think I started in 1999.
00:07:08.280 | Every kid had a laptop and everything was online.
00:07:12.200 | You were like, if a teacher emailed you an assignment and you didn't get that
00:07:14.840 | email, like you're failing the assignment.
00:07:16.600 | That was kind of new at that age for a school to do that.
00:07:19.560 | And it was super old school.
00:07:21.000 | Like all the computers still needed ethernet.
00:07:22.680 | So every single desk and every single classroom had an ethernet plug and you
00:07:25.960 | had to like plug your laptop in and you had to charge it because the battery
00:07:29.280 | only lasted like 45 minutes.
00:07:31.120 | We actually had a class where you could become a Microsoft certified network
00:07:35.360 | administrator that took that class.
00:07:37.640 | And we had a network.
00:07:38.920 | And I remember in high school, we wanted to like share games and
00:07:43.080 | movies that we'd all downloaded.
00:07:44.600 | And so we created like a network that you could log into.
00:07:47.400 | That was our network, right?
00:07:48.560 | Like there was the school network you could log into.
00:07:50.360 | And then me and these three, four guys created our own network that you could
00:07:53.400 | log into and share stuff.
00:07:54.960 | In high school, this friend of mine sent me this email and was like, "Hey, I met
00:07:58.000 | these guys that are selling dial-up internet service.
00:08:01.560 | You can sell it for them and make a lot of money.
00:08:04.960 | Do you want to learn about it?"
00:08:06.000 | Sure.
00:08:06.600 | So I go to this meeting and they're pitching this thing that they're like,
00:08:09.520 | "Yeah, we sell dial-up internet service."
00:08:10.880 | But like, that's not the cool thing.
00:08:11.920 | The more reps you sign up under you to sell dial-up internet service,
00:08:16.200 | the more money you make.
00:08:17.240 | This is a total pyramid scheme.
00:08:19.520 | So instead of walking away, I was like, "Gosh, what should I do?"
00:08:22.680 | I like called up Fox 5 in DC and was like, "I need to talk to the
00:08:26.840 | investigative reports team.
00:08:28.360 | I've got something for you."
00:08:29.760 | And we ended up bringing a, like an undercover camera.
00:08:34.160 | I had like a camera on a button on my shirt and we hid another camera in a room.
00:08:37.920 | And I had a fake brother or cousin.
00:08:41.200 | I can't remember who I was.
00:08:42.160 | I emailed them.
00:08:42.800 | I was like, "Hey, I don't know how I feel about the pitch, but my brother's obsessed.
00:08:46.400 | You guys got to come talk to him."
00:08:47.960 | And we did like an undercover sting operation where we exposed the pyramid
00:08:52.360 | scheme and all that kind of stuff.
00:08:54.160 | And ultimately, that company never existed.
00:08:56.040 | I guess a theme in my life was if something can't be done, let's just try it anyways.
00:09:00.400 | Boarding school had really prepared me to not have to deal with all of the stress
00:09:06.080 | that comes from living away for the first time when you go to college,
00:09:08.840 | figuring out what that's like.
00:09:10.080 | And so when I got to college, I was like, "Let's do all the things."
00:09:13.720 | And so I remember a lot of the kids I went to high school with were always
00:09:17.120 | posting online and this is like early days of Facebook where like the only
00:09:21.240 | thing you do is post what you're doing.
00:09:22.640 | And so people were like, "Oh, I'm at this concert."
00:09:24.680 | And I was like, "How are you going to this concert?"
00:09:26.240 | They're like, "Oh, our school put on a concert."
00:09:27.760 | And I was like, "What do you mean your school?
00:09:29.640 | My school doesn't put on concerts.
00:09:31.000 | And if we do, there's certainly nothing anyone wants to go to
00:09:33.600 | or they're not that exciting."
00:09:34.960 | So I was like, "Hmm, I wonder how you can do that."
00:09:37.160 | And I was in student body government at the time.
00:09:39.120 | I was like, "Oh, you know what?
00:09:40.560 | Anyone can rent the stadium, like the basketball stadium at school.
00:09:44.160 | Anyone could get permits to reserve the parking lots."
00:09:47.920 | So I was like, "Oh, what if I just put on a concert?"
00:09:50.760 | I talked to a friend of mine who was like way more into music than I was,
00:09:54.560 | at least more mainstream music.
00:09:56.040 | "Dude, what's the band that we should do a concert for?"
00:09:58.560 | And he's like, "I got this band and they're going to be huge.
00:10:00.920 | They're called The Fray."
00:10:01.800 | I have no idea what that means.
00:10:04.400 | And he's like, "They're really good.
00:10:05.720 | I'm going to go on a limb and trust you because I have no idea what this band is."
00:10:09.680 | But thanks to my trusty friend, Kevin, that we booked The Fray.
00:10:13.880 | And then we went to the school and we're like, "We need to rent the stadium.
00:10:16.800 | Can you guys sell tickets for us?"
00:10:18.520 | So we ended up selling tickets.
00:10:19.720 | We ended up putting on this concert, but we didn't hire a production company.
00:10:23.680 | We did for lights and sound, but not for making the whole event work.
00:10:28.440 | VIP backstage passes were things that I printed on my printer in my room.
00:10:33.440 | And I bought a laminator to laminate them.
00:10:36.080 | And when we had to make a green room, we literally took couches from our apartment.
00:10:40.360 | We went to Walmart to buy the stuff people asked for in their riders.
00:10:45.080 | It was the most amateur experience you could imagine, but it all went off.
00:10:50.520 | And I think we probably made like five grand, which in college was the most
00:10:54.440 | amazing amount of money ever split between three or four people.
00:10:57.560 | And it's a theme in my life that I guess sometimes gets you into trouble, but
00:11:01.000 | oftentimes leads to exciting things.
00:11:03.520 | I've asked in almost every company I've worked at, "Let's go meet with the CEO.
00:11:07.120 | Let's go meet with the person running this team."
00:11:08.920 | And I've been told sometimes, "Oh, you can't do that."
00:11:11.600 | I'm like, "Why not?
00:11:12.280 | I'm just going to try."
00:11:13.080 | So in college, I was like, "I'm just going to go schedule a meeting with
00:11:16.080 | the Dean of the business school."
00:11:17.880 | And I didn't know until later that he's on a bunch of boards, knows a lot of
00:11:21.600 | companies, the deans of colleges and the people who run the school,
00:11:25.560 | they're pretty connected.
00:11:26.400 | So I was just like, "Well, I'm going to go meet with them."
00:11:28.240 | It wasn't a thing that most people were doing, but it turned out to be the only
00:11:31.880 | reason I got a job after I graduated.
00:11:33.920 | That might be actually one of the best college indirect advice I've ever heard.
00:11:38.920 | Try to make a relationship with the Dean, introduce yourself when you get there.
00:11:42.880 | That is the first, I'm 37 years old.
00:11:45.040 | That's the first time I'm like, "Oh, that would have been actually smart.
00:11:48.200 | I should have done that."
00:11:49.120 | I never really knew what I was going to do after college.
00:11:51.680 | You know, what ultimately happened was I went home over Thanksgiving and I
00:11:56.520 | connected with a bunch of friends that I went to middle school and high school
00:11:59.280 | with, and they all had jobs.
00:12:01.320 | And I was like, "What do you mean you have a job?"
00:12:02.680 | And they're like, "This is when all the companies hire.
00:12:05.200 | Like, if you want a job at top companies, it's gone."
00:12:08.400 | And so I went back to school after Thanksgiving, before Christmas, and I
00:12:12.040 | went to the Dean and I said, "Hey, I need a job in management consulting or
00:12:16.680 | investment banking.
00:12:17.480 | Can you help me?"
00:12:18.160 | He came back.
00:12:18.920 | He said, "I know a guy who works at one management consulting firm and I sit on
00:12:23.800 | the board of this company.
00:12:24.720 | And there's another guy on the board that works at an investment bank."
00:12:27.520 | He's like, "I'm going to introduce you to two of them."
00:12:29.680 | Sure enough, I hear from the management consulting firm, "Yeah.
00:12:33.040 | You missed the boat.
00:12:33.800 | The cycle to get a job after graduation is over.
00:12:36.480 | But if you want to interview, you can interview for the next cycle."
00:12:39.280 | And I was like, "Great.
00:12:40.000 | Let's do it.
00:12:40.360 | Bring me in."
00:12:41.000 | So I came in, I interviewed there.
00:12:42.480 | And then the investment bank said, "We don't hire people out of college, but we
00:12:46.560 | have an internship that you could do.
00:12:48.240 | And if it works out, maybe it turns into a job, but probably not."
00:12:51.840 | Fortunately, at the end of the internship, they offered me to stay on.
00:12:55.320 | But it wasn't stay on, you're now on the same ranks as all of the associates.
00:13:00.400 | It was like stay on as a full-time intern kind of thing.
00:13:03.720 | But instead of having a class of 20, where I had 19 other people to help out with all
00:13:07.960 | the work they wanted the interns to do, it was just me.
00:13:11.240 | My breaking point was a week where I didn't see my wife awake.
00:13:15.400 | At the time, girlfriend, I didn't see her awake for five days straight.
00:13:19.000 | And I went to management consulting.
00:13:21.800 | I guess I thought it would be a lot different, but it was pretty similar.
00:13:25.960 | Maybe swapping out Excel for PowerPoint.
00:13:28.680 | In management consulting, it's all about slides.
00:13:30.640 | In investment banking, it's all about spreadsheets.
00:13:32.360 | But my experience in management consulting was one where I really understood what an
00:13:40.440 | entrepreneurial spirit is and how it can be crushed.
00:13:43.040 | It's a job that provides you a ton of access to interesting problems and really smart
00:13:48.200 | people, but it's not a place in most firms or the firm I was at where if you have an
00:13:53.760 | idea that could be really interesting at a more senior level, that you could do that.
00:13:58.520 | Science has shown that being charitable can actually have a huge impact on your
00:14:04.160 | happiness, which is why I'm excited to be partnering with Daffy today.
00:14:07.840 | They're a not-for-profit community built around a new modern way to give, and they
00:14:12.240 | have a mission I think we can all get behind, helping people be more generous more
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00:15:15.520 | So I am quite comfortable right now, which is actually true almost every day, and
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00:15:29.720 | designed to work out in, but it doesn't look or feel like it at all, and it's so
00:15:33.960 | freaking comfortable, you will want to wear it all the time. Seriously, I am
00:15:37.800 | pretty sure it's more comfortable than whatever you're wearing right now, unless
00:15:41.280 | you're wearing Viore, in which case you already know what I mean. And it's not
00:15:44.840 | just for men. My wife is as obsessed with Viore as I am. My favorite is the Sunday
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00:15:57.800 | activity, whether it's running, training, or yoga. They're also great for lounging,
00:16:02.440 | running around town, or their Meta Pants can even work for a night out. Honestly, I
00:16:07.280 | think Viore is an investment in your happiness, and for all the Hacks
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00:16:33.480 | comfortable and versatile clothing on the planet. Then one weekend, I heard
00:16:37.800 | about an event called Startup Weekend that a guy named Andrew Hyde started, and
00:16:41.320 | everything for the rest of my life changed in like a flash. And that was in
00:16:45.840 | October 2007. So despite living in New York City at the time, I knew the
00:16:51.400 | financial crisis was happening, but it didn't really hit me until a year later.
00:16:54.240 | But Startup Weekend was crazy. I drove up to Boston. This event had happened in
00:17:00.520 | Boulder. I don't even know how I heard about it. And I drove up to Boston. I
00:17:04.480 | didn't even have a place to stay. I was like, "I'll sleep on the couch. It
00:17:07.240 | doesn't matter. This sounds cool." And the idea was get together engineers,
00:17:11.480 | designers, product people, just anyone. And in the weekend, let's start some
00:17:15.440 | companies. So I joined this team and we built a product called Desk Happy. And it
00:17:19.720 | was a Windows app that every some odd number of hours would remind you to
00:17:25.280 | stretch or stand up or do anything. It reminds me of like the Apple Watch
00:17:29.800 | pause to breathe kind of thing. But back in 2007, and it didn't go anywhere.
00:17:34.360 | Like 250 people used it. And I'm fairly certain that they were all the
00:17:38.080 | friends and family of the people that were in the room. But I realized, "Wow, in
00:17:42.200 | 48 hours, we built a company that makes a product online that people could
00:17:46.720 | buy if it were actually good. And obviously, we didn't spend that much
00:17:49.560 | time on it." This is crazy. This is a job. What I'm doing right now, helping build a
00:17:55.280 | product is a thing I could do for a living. I was like, "What am I doing with
00:17:59.400 | management consulting?" Andrew was like, "Oh, I'm doing another one in San
00:18:01.920 | Francisco." I was like, "I'll be there." And while we were there, I ended up
00:18:04.600 | meeting some really fascinating people. And I was like, "I gotta do this." I came
00:18:08.680 | home and I was like, "Amy, you don't even love living in New York. How would you
00:18:13.920 | feel about moving to San Francisco?" So Amy, my wife, who is incredible and has
00:18:19.520 | supported me through, I don't know, like 10 different jobs and experiences. And we
00:18:24.240 | met sophomore year in college.
00:18:26.280 | Hello, I'm Amy.
00:18:27.880 | We didn't get married for a while. I think in our minds, it was like, "We just
00:18:30.400 | have so much going on. We don't know where we're going to live." We were very
00:18:33.280 | practical about it saying like, "Look, we need to make sure that we're living in a
00:18:36.800 | place that we both want to live for a long time." She grew up in Colorado. I
00:18:40.840 | grew up in DC. In New York, we're like, "We don't want to live in New York
00:18:43.600 | forever." And San Francisco ultimately ended up being that. She felt like New
00:18:47.800 | York wasn't the place for the long term. And the company I worked for only had
00:18:52.080 | offices in Chicago, New York, Boston, San Francisco, and LA. We came up with
00:18:56.200 | reasons that the other cities didn't work. And she didn't love her job at the
00:18:59.640 | time. So we were like, "Great, let's move. And at least I'll be able to keep my
00:19:03.600 | job." And then we were like, "Okay, we should probably find an apartment." And
00:19:07.000 | then like, a week later, I get this message to come to the office and have a
00:19:12.680 | meeting with a person I've never met before, who ultimately laid me off. This
00:19:16.880 | was October 2008 by now. It had been a year of startup weekends, trying to
00:19:21.160 | figure out how to move, moving out. It didn't all happen in a week. But we were
00:19:25.640 | in the middle of the financial crisis. This was a major situation. I was like,
00:19:29.920 | "Look, I moved to San Francisco to go work in tech. I didn't move here to work
00:19:32.720 | in manager consulting forever." So I was ready to leave. We're trying to figure
00:19:35.320 | out what to do. I have no job. No one's gonna hire you between Thanksgiving and
00:19:39.800 | Christmas. Companies are closed. Also, no one's gonna hire you because the entire
00:19:43.320 | economy is crashing. It was definitely a blessing in disguise because I ended up
00:19:49.440 | getting to find all the crazy cool stuff that ended up following. But I was
00:19:53.880 | kind of pissed. It's like, "You just let me go right in the middle of the
00:19:57.400 | holidays." And one of the things that I ended up doing was going to South by
00:20:01.560 | Southwest. I went to this event at South by Southwest called Bar Camp. The idea
00:20:06.000 | was you create this conference and people just make up topics on the fly.
00:20:09.600 | They were kind of mostly technology-related. People are like
00:20:12.320 | creating events, but there's no organizer. Flashback to the days that we put on a
00:20:16.920 | concert in college on our own. It was like we put on a conference on your own. You
00:20:20.880 | just say when whoever shows up writes on a sticky pad, "This is a topic I could
00:20:26.720 | lead a discussion about or teach people about." You create a schedule on the fly
00:20:29.960 | of what the day is. And it occurred to me that there are so many people that are
00:20:34.400 | unemployed right now and I'm one of them. Options are find a job, start a company,
00:20:40.120 | start freelancing. And I knew nothing about any of those things. It's like, "What
00:20:43.640 | if we just put on an event? Let's call it Laid Off Camp." And next thing you know, I
00:20:47.440 | put on an event with the help of a lot of other people, with hundreds of people
00:20:52.000 | showing up, with the media from all over the country. Being laid off can feel
00:20:57.160 | pretty lonely, sitting at home searching the internet for jobs, worrying about the
00:21:01.800 | future. It's called Laid Off Camp and it feels a little like camp. It's very find-a-job 2.0, I guess.
00:21:09.080 | Maybe it's the idea of camp, even if it is for laid-off people. It's taking place
00:21:13.680 | at a club in downtown San Francisco, so there's white leather couches and
00:21:17.420 | music. It just like really captured the spirit of where the economy was in a way
00:21:22.880 | that I never anticipated. And it was totally open-source. So I actually
00:21:26.720 | created a website that was a wiki. I said, "If you live in another city and want to
00:21:30.880 | do this, here's the email I sent to sponsors. Here's the schedule. Here's how
00:21:35.080 | I organized it." And there ended up being 20 of them around the country. And it was
00:21:38.600 | very temporal. The economy kind of recovered, people got jobs, and it kind of
00:21:43.040 | just withered away. And Laid Off Camp is no more, which is totally fine. But it was
00:21:47.960 | an awesome chance to meet lots of people. And it was a huge opportunity to kind of
00:21:53.520 | grow in a city that I had only been in for a very short period of time, but very
00:21:58.800 | quickly wanted to try to immerse myself in. So after that, you would think the
00:22:04.800 | story would most logically be, "I met these companies. I started working for
00:22:08.960 | them. And I had all these fun jobs, but it's a little different." So a company
00:22:14.320 | said, "Hey, you put this event on. We want to put on an event to engage our users
00:22:18.240 | and our clients. Could you help us put on a series of events?" And I was like,
00:22:21.360 | "Cool." So I worked with this company outright. Another company came to me and
00:22:24.280 | said, "Hey, we're trying to do a... I think it was like a Series C fundraise,
00:22:27.400 | which now it's probably like a Series F." One of their investors said, "Hey, can you
00:22:30.880 | put together some financials of what's going on in your business?" And they had
00:22:34.920 | no experience doing that. And they were like, "Hey, you used to work at an
00:22:37.920 | investment bank. Can you help us?" So I was working with this company called
00:22:41.560 | User Voice to put together their financials and their projections in
00:22:45.920 | their pitch deck for their fundraising. I didn't love freelance work because it
00:22:49.760 | was very much, you don't have the end ownership in the project. But at the
00:22:53.840 | time, in the wake of the financial crisis and not knowing where I would
00:22:56.480 | work, it was great to have an income. It all comes to an end. However, any
00:23:00.560 | freelance gig usually has an ending. And so I was, I guess, unfortunate and
00:23:05.560 | fortunate that they were all coming to an end at the same time. So normally, you
00:23:09.280 | try to stagger these things out. So if you have 3 clients and you go to 2, you
00:23:12.440 | can get a third. Well, I went from 3 to 0 in like a month. But I knew it was
00:23:16.480 | coming. And so a month out, I asked my wife, I said, "Hey, if I'm gonna have no
00:23:20.640 | job for a month, should we take a trip?" I put a lot of the expenses from laid-off
00:23:24.600 | camp on my credit card. I'd become like an optimizer. So I'd signed up for
00:23:28.320 | different cards to get signup bonuses. So we had some miles. I was like, "Let's
00:23:32.200 | take a trip." And my wife said, "Let's do it." So we bought a map. We put it on
00:23:35.760 | the wall. And we bought push pins. And we're like, "Let's put some push pins in
00:23:39.720 | the countries that we're excited to visit." There were so many pins. We were
00:23:43.600 | like, "How are we ever going to do this?" Cluster them together. We're like, "Oh,
00:23:46.360 | if we want to go to these 2 countries, that's a 2-week trip. We want to go to
00:23:49.400 | these 2 countries, that's a 2-week trip." As I was doing all this research on
00:23:52.160 | which countries to go to, I found people that were like, effectively, they quit
00:23:56.280 | their job. They did a gap year. They became nomads. They went on these
00:24:00.400 | extended trips. And I was like, "That's interesting." And if you look at any
00:24:05.440 | trip that you've been on, the main cost of a trip is usually getting there. The
00:24:10.480 | flights are the big cost. The lodging would be the second biggest. We realized,
00:24:14.880 | "Wow, if we could stay with interesting people around the world, and we could
00:24:18.320 | travel slowly, meaning take a bus between 2 countries for $1 instead of a
00:24:22.920 | flight for $300, the trip wouldn't actually cost that much more. And we could
00:24:28.040 | sublet our apartment." And all of a sudden, we realized, "We're taking a long
00:24:32.040 | trip." And so we decided, "Let's quit. Let's take a trip." So we ended up
00:24:36.480 | flying one way to South Africa. And over the course of 8 months, we trekked up
00:24:42.400 | Africa, through the Middle East, and through Southeast Asia and India. We
00:24:46.640 | probably spent I think $7,000 each for an 8-month trip around the world. If you
00:24:52.160 | do the math and you take $7,000 and you divide it by 8 months... We're talking
00:24:57.600 | about $30 a day. So that's food, that's activities, that's transportation. So we
00:25:03.080 | were finding crazy ways to take a 52-hour train ride from Zambia to Tanzania.
00:25:09.240 | I've always been a person that's looking for the best deal. And I try to go back
00:25:13.760 | to figure out where that started. My dad definitely played the points and miles
00:25:17.760 | game. And we would take trips as a kid in business class using his miles to Europe.
00:25:22.480 | So I always knew that existed. I was always trying to figure out, "What's a
00:25:26.000 | way to get what I want without having to spend money?" And in college, that was
00:25:31.160 | opening up credit cards for bonuses, to be able to take trips for free. And on
00:25:34.920 | this trip around the world is where it kind of... It was just like a daily
00:25:38.400 | occurrence because we had no money. We had money to go on this trip. But if we
00:25:43.640 | spent it all, we had to go home early. We knew we had enough miles to get a one-way
00:25:46.880 | ticket back home from anywhere in the world. So we knew at some point we would
00:25:50.800 | go home. But the more optimal we could be, the longer we could go. And so we were
00:25:56.160 | couchsurfing almost the whole trip. We found people on a Lonely Planet forum on
00:26:00.040 | the internet who also wanted to travel around Namibia and Botswana. And we
00:26:04.360 | rented a car. We bought a used tent and some sleeping bags. And the 4 of us, my
00:26:09.800 | still-not-yet wife and girlfriend, and 2 guys from Sweden shared a
00:26:15.200 | 3-person tent and rented a Toyota Yaris and drove around Southern Africa
00:26:21.260 | and a few countries. And so we were always trying to be super optimal. I came
00:26:25.440 | back and everyone was like, "How did you do that?" Every person you talk to when you
00:26:28.920 | say, "I took 8 months. I went around the world. I saw these amazing things and I
00:26:32.080 | spent $7,000." They're like, "I want to do that." After that trip, it was just like my
00:26:35.440 | identity. I remember one of the things I did right as we were leaving. Submissions
00:26:40.760 | were due to speak at South by Southwest. And I was like, "Gosh, the next step
00:26:45.040 | for me is to build a network in a more elevated sense in this tech
00:26:50.800 | community." Because I knew whenever I came back, I want to work in tech. I want to
00:26:53.680 | work at a startup. So I was like, "Man, if I could speak at South by Southwest, that'd
00:26:57.000 | be really cool." So I submitted this talk about what it's like to be unemployed
00:27:00.280 | and start things. It was called Fun Employment in the Wake of the Crisis or
00:27:04.160 | something like that. So I was in Turkey and we were literally sitting in a
00:27:07.680 | guest house carved into the side of the mountains of Cappadocia. But they had
00:27:12.400 | internet and I logged on. It was like, "Your talk was approved." And I was like,
00:27:15.680 | "What? Really?" I thought it was a big long shot. But I was like, "I'm gonna be a
00:27:19.200 | speaker at South by Southwest. This is next level." We have 4 or 5 months
00:27:23.360 | left, but March is when it ends. And we were like, "The end is Singapore. You
00:27:27.920 | get to Singapore." So we were like, "Great. I'm gonna book a flight from Singapore to
00:27:31.320 | Austin. And I'm gonna go to South by Southwest straight from the trip." And I
00:27:35.680 | now have this new mission, which is I am going to work for whatever I can find to
00:27:40.720 | be the hottest startup there is. I want to work for a name brand, amazing
00:27:44.880 | startup. That is my mission. South by Southwest is my opportunity to find it.
00:27:49.440 | All these founders and investors are here. This is what my new life is.
00:27:53.840 | I was convinced that I found it. I found this company called Simple Geo right
00:27:58.840 | after the iPhone 3GS came out. So we all had mobile phones and they had GPS, but
00:28:03.840 | nobody really knew what to do with it. And their whole idea was "We're gonna
00:28:06.720 | build software that enables developers to use location in their products." I had
00:28:13.080 | met casually one of the founders. I wasn't sure how to do this. So I made
00:28:16.880 | this presentation that was all about the industry and what's happening and the
00:28:20.520 | opportunities. And I had one person I knew well enough who was an investor in
00:28:24.600 | the company. I was like, "Can you send this to the founders and let them know? I
00:28:28.280 | would love to talk to them." At the time, I thought this is a long shot. I now
00:28:32.320 | realized that if a person is that excited to work for you, just hire them.
00:28:36.240 | So I worked full time at this company in business development. But ultimately,
00:28:40.800 | the startup didn't work. Around the same time, I had connected with a couple
00:28:44.800 | people who had started and worked early at a company called Digg, which was
00:28:49.520 | like Reddit before Reddit. They were starting a new company. It was so early.
00:28:53.080 | This was pre-really starting. And they were like, "Hey, do you want to come
00:28:55.640 | join our founding team? And we're going to build this incubator to build
00:28:59.760 | products." And I was like, "Gosh. Yeah, of course."
00:29:02.520 | By the time I was joining Milk, I felt like I had a good sense of the
00:29:07.880 | community and the products and the companies in that aspect. But I had no
00:29:11.600 | clue really how to build a consumer product. SimpleGeo was building an API
00:29:17.640 | dev product, but they were not building something for consumers. So now it's
00:29:22.120 | this whole new world of, "Well, I got to do customer research. I've got to
00:29:24.840 | figure out how things work." And so Milk was my chance to learn how to build
00:29:28.240 | consumer products. So I came in and I don't even know what my job was at the
00:29:32.520 | time. I was in charge of HR, payroll, BD, partnerships. I was learning
00:29:39.680 | everything. I didn't know how to set up payroll. I didn't know how to give
00:29:42.080 | benefits for a company. I don't know how to do any of this, but I was like, "I'm
00:29:45.200 | going to learn and I'm going to ask everyone I can for advice." And
00:29:48.720 | throughout that experience, I was like, "Wow. I feel like I accelerated my
00:29:52.480 | ability to hold my own in the tech community and found a home, at least
00:29:57.920 | a... I think I found a home of building products was really cool."
00:30:02.320 | But we were trying to figure out how to make the model work. We built a
00:30:04.800 | product that was pretty cool. And we were in this crossroads of, "Do we try
00:30:09.480 | something new? We're an incubator. Do we double down on the thing we built,
00:30:12.880 | which we didn't have enough conviction to do? Or do we take all the skills of
00:30:17.080 | what we learned and apply them at a bigger company?"
00:30:19.960 | We had the opportunity to do that at Google. And so we sold the company to
00:30:22.440 | Google. Going through that negotiation, I was frantically trying to make sure
00:30:26.360 | all the pieces were in the right place and organizing all the diligence
00:30:29.000 | information. And when we landed at Google --and this is so silly-- was that
00:30:34.360 | finally, people who didn't work in tech had some sense of what I do.
00:30:39.160 | Like, "I'm working at this startup that you've never heard of." "Oh, okay."
00:30:42.600 | You go to family reunions, people don't believe that you even have a job.
00:30:46.040 | They're like, "What are you doing?" And now I'm like, "I work at Google."
00:30:48.840 | And they're like, "I know Google. I search for things with it." It relates.
00:30:53.000 | So I go to Google. And through the interview, they're like, "You are a
00:30:56.280 | product manager." I didn't know where I would get placed through these
00:30:59.400 | interviews. I said, "You're a product manager."
00:31:01.640 | So I tried my hand at product. It was a frustrating experience because I was
00:31:07.000 | working on Google+, which was a project that, at the time, had about 100 product
00:31:13.720 | managers and 1000 total people working on it.
00:31:16.520 | And my running joke has always been that at any given point in time, there were
00:31:20.120 | more people working on Google+ than using it. We were trying to figure out if
00:31:23.560 | there was a better place at Google that we could spend our time.
00:31:27.080 | And I had raised $250,000 for milk from Google Ventures.
00:31:31.880 | So I went to the team that we raised money from and I said, "Hey, you guys all
00:31:35.880 | work at Google. You probably know this org better than we do. We've only been
00:31:38.600 | here a few months. Where should we work?"
00:31:40.680 | And then they came back and they're like, "Actually, you and Kevin have very
00:31:43.880 | distinct skill sets. Kevin's been a very successful seed investor.
00:31:47.240 | And you're at every event in the mix with everyone. And that's not something
00:31:51.720 | we'd really been doing. We'd been really focused on a different style of
00:31:55.480 | investing. Why don't you come and do seed investing here?"
00:31:58.280 | We moved over to Google Ventures. And for the first time in my life, I had a
00:32:02.040 | job that lasted for more than one year.
00:32:03.560 | I wish I could say that I'm eating a fully balanced diet every day, but the
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00:34:31.880 | I just want to thank you, Kwik, for listening to and supporting the show.
00:34:35.560 | Your support is what keeps this show going. To get
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00:34:42.840 | you can go to allthehacks.com/deals. So please consider supporting those who
00:34:48.600 | support us. Now I'm about to go into venture
00:34:50.760 | capital, right? I'm about to pick startups and I'm reflecting on my ability to do
00:34:54.200 | that, having, you know, joined a startup that
00:34:56.360 | didn't work, joined another startup that didn't work but fortunately got acquired.
00:35:00.280 | Meanwhile, if we rewind to coming back from the trip around the world,
00:35:04.760 | the talk I gave at South By was with a friend of mine named Matt Van Horn,
00:35:08.200 | who at the time also worked at Digg. He had a friend that I think was a friend
00:35:11.720 | from college or maybe from childhood that was starting this company called
00:35:14.360 | Zimride. They basically replaced that message
00:35:17.320 | board that we had in college, if you're old enough to remember, where you were
00:35:20.520 | like, "Hey, for Thanksgiving, I'm driving here. Does
00:35:22.920 | anyone want to get a ride?" And we didn't have some cool app to do
00:35:25.720 | it with. And so they were long-distance ride-sharing. It was
00:35:29.080 | replacing like going on Craigslist and being like, "Who wants to drive to LA
00:35:31.880 | this weekend and split gas?" And for some reason, I was like, "I'm not
00:35:35.080 | that interested in this company." But they were also hiring people in
00:35:38.600 | sales. And so I told my wife, I was like, "Hey, you should meet this company."
00:35:41.880 | And we'd just gotten back from this trip. She didn't have a job. She ended up
00:35:45.080 | loving the team and joining as one of the first... I think
00:35:48.600 | she was number five on the team at Zimride.
00:35:51.080 | And the irony in all this is my mission coming back from this trip
00:35:55.400 | was to pick the hottest startup in Silicon Valley. And I met the guys at
00:35:58.760 | Zimride. I was like, "This is not the hottest startup.
00:36:01.160 | I'm going for SimpleGeo. SimpleGeo is the one."
00:36:04.280 | So for those who don't know, Zimride became Lyft.
00:36:07.160 | My wife ended up working at Lyft for 10 years, getting arguably
00:36:10.680 | an even more advanced and accelerated learning experience than I did
00:36:14.840 | watching a company go from 5 people to a public company.
00:36:18.760 | And then now here I am going into Venture Capital, where my job is to pick
00:36:23.400 | which company will be successful. And yeah, I'm working at Google Ventures.
00:36:27.160 | And I was there for 3 years.
00:36:30.760 | Boy, it was the most fascinating thing in the world to be able to sit in on
00:36:34.520 | these pitches of late-stage companies, hear the questions that smart people
00:36:38.440 | that I worked with were asking. And I thought, "Wow, this is finally my
00:36:41.800 | opportunity to work at a company for more than one year."
00:36:44.600 | This all ties into money in a weird way. I'm still wildly frugal at this
00:36:48.360 | point in my life and now as well. But all of that, I think,
00:36:52.120 | stems from the fact that I keep having jobs that I never truly knew that I
00:36:56.760 | could do forever. One year into Venture Capital, I'm really
00:36:59.160 | enjoying it. Maybe I can spend money now because I know that there will be
00:37:02.840 | money coming in the future. My worry my whole life was I could never
00:37:06.040 | find a thing I love doing. And if I couldn't,
00:37:08.040 | I didn't want to do something I didn't love, so I wouldn't have money.
00:37:11.240 | So I was aggressively pursuing financial independence, trying to save every
00:37:15.320 | dollar I could because I didn't know that there was a thing I could do that
00:37:19.240 | made me happy that generated an income. But 2 or 3 years in, I think, "Gosh,
00:37:25.240 | this is fun, but I just don't know if this is for me forever."
00:37:29.080 | It wasn't that Venture Capital wasn't fun or it wasn't learning,
00:37:31.960 | but I think I had this thing inside me that I don't anymore think is true.
00:37:35.960 | But at the time, I thought, "How can I go invest and help these companies
00:37:40.120 | if I've never actually done it myself?" I've never been the CEO of a company.
00:37:43.960 | I've never seen it through. Inside, I was like, "I can't do this
00:37:47.400 | forever. I can't move out of seed and do later stage investing if I haven't
00:37:51.000 | been there and done that." A problem that I noticed everyone
00:37:54.120 | having and they're coming to me. They know that I'm obsessed with personal
00:37:56.680 | finance. So everyone's asking me what to do with money. They're like, "Hey,
00:37:59.320 | we're getting married. What do we do? Do we combine our finances? Hey,
00:38:01.960 | what do we do with our savings? We actually have money. Hey, we're thinking
00:38:04.280 | about buying a house. Should we do that? How much house can we afford?"
00:38:07.480 | And I'm like, "God, people don't know what to do with their money."
00:38:09.720 | And the more I learned, nobody knows what to do with their money.
00:38:12.280 | So I was trying to figure out what could solve that problem.
00:38:14.760 | And I heard about this practice that exists called financial planning,
00:38:19.800 | which was different from managing your investments. It's about creating this
00:38:22.920 | comprehensive plan. And I was like, "Wow, this is interesting. I wonder
00:38:26.040 | if that process of going through a financial planning process would solve
00:38:31.000 | all these problems these people keep coming to me with about money."
00:38:34.280 | Everyone should have a financial plan. Everyone's dressed out with money.
00:38:37.720 | Everyone should have a financial plan. How do we solve that? And I connected
00:38:41.160 | with the friend from middle school, who we built dungeon games on our
00:38:44.520 | computers. We'd been talking about this. And every time someone had questions,
00:38:47.560 | he was my like, "Okay, let me think about that and get back to you."
00:38:50.440 | So he decided to move to California.
00:38:53.560 | He lived in our spare bedroom. And we were like, "Let's start this company.
00:38:58.440 | If it works, and if we can raise a Series A."
00:39:00.840 | He's like, "I'll talk to my wife and we'll move to California.
00:39:03.560 | But if we can't, I'll just go back."
00:39:05.800 | And so ultimately, we left. I told Google Ventures, "I got to work on this more."
00:39:10.680 | Thankfully, my wife was now at a much later stage lift,
00:39:14.600 | had a much more stable income, and could support effectively going all-in on,
00:39:19.160 | "Let's do a startup. Let's found it. Let's be the CEO. Let's be the one in charge."
00:39:23.640 | Step one, we had to see if the product works. So we just made a product.
00:39:26.760 | We created a registered investment advisor. We went through the regulatory filings.
00:39:31.240 | We started helping people to prove that this worked
00:39:33.880 | and collecting enough data that ultimately, we were able to raise money.
00:39:37.640 | And so we pitched investors.
00:39:39.720 | The way seed investing often worked, at least at the time,
00:39:42.840 | was that there were a lot of funds that didn't want to leave.
00:39:44.760 | So people were like, "I'm kind of interested, but I'll get back to you."
00:39:48.120 | And all it took was a lead. And if you didn't have a lead, everything fell apart.
00:39:51.800 | So we dug in. I remember my co-founder and I sitting at my dining room table
00:39:56.200 | where we were working, saying like, "Gosh, if this doesn't work by next week,
00:39:59.800 | I think we wrap it up, call it done."
00:40:03.080 | And then an hour later, I finally get the call from first round.
00:40:06.360 | They're like, "We want a lead."
00:40:07.320 | And so fast forward, a fun process that now that you have a lead and it's a good lead,
00:40:14.040 | everyone else is like, "Oh yeah, I'm totally in. I know I did. I said I wasn't sure,
00:40:17.160 | but now I'm in."
00:40:18.280 | And so now we were like, "Oh, how do we put this around together? How much is it?
00:40:20.680 | How do we fit everyone in?"
00:40:21.640 | And we went down a totally different path. Co-founder decided, "Okay, we're going to move
00:40:25.320 | out." His wife, he and his wife moved out. They still live out here in Palo Alto.
00:40:29.560 | He's now working at Stanford. And so we have a round.
00:40:32.600 | And we're like, "We're off to the race. We got to hire people. We got to get an office."
00:40:35.560 | And we scaled up a team. We continued building a product. We launched.
00:40:39.560 | We had a waitlist that was longer than we could handle.
00:40:42.920 | But in raw numbers was hundreds of people. And we had proven hundreds of people were
00:40:48.120 | willing to pay us. We had a paid waitlist to use our product.
00:40:51.400 | But when we finally had the capacity to take people off the waitlist,
00:40:54.680 | they all said, "I'm not ready yet."
00:40:57.400 | And we're like, "Oh, do you want your money back?"
00:40:58.520 | And they're like, "No, no, no. Keep the $50. I want to do it. I just want to do it right now."
00:41:02.200 | The lesson we learned brutally over the next year was that everyone wants financial planning,
00:41:09.400 | but nobody wants to do it right now. To scale customer acquisition beyond that
00:41:14.040 | group of 1,000 people that really wanted it now, there was latent demand of people like,
00:41:18.440 | "I just want this and at a lower price. It's amazing." We just couldn't scale it.
00:41:22.120 | $4 million still in the bank. We realized human-powered financial planning
00:41:28.040 | is not a product that you can lead with. If you want to do it at scale, it has to be
00:41:33.000 | a complementary product to something that has an urgency of using now.
00:41:38.200 | And I was also thinking at the time with my co-founder that maybe we don't need humans.
00:41:43.000 | Maybe you could implement all this in software. We still would have the problem that if people
00:41:47.640 | aren't ready for it now, but we are starting to come to the conclusion that maybe that would be
00:41:51.160 | possible. We weren't sure. And around the same time, I had a conversation with Andy Ratcliffe,
00:41:56.920 | who was running Wealthfront. And he said, "Look, we have this vision for self-driving money.
00:42:00.440 | We want to automate all of the financial planning and everything.
00:42:03.720 | We'd love people to come help work on that." And we're like, "This is a great opportunity."
00:42:08.600 | And I've spent the last 2.5 years working on all kinds of other personal finance products
00:42:14.600 | at Wealthfront, trying to ultimately solve the same problem, which is to help people
00:42:18.440 | make growing their wealth easier. Meanwhile, while all this is happening,
00:42:22.680 | I still haven't convinced myself that I found a job I can work at forever. Because the startup
00:42:28.280 | was not working. Now I'm at Wealthfront. And so I still have this thing in my core, which is
00:42:34.920 | you still need to keep optimizing to save money. But I still want to do crazy fun stuff.
00:42:41.160 | And so I'm constantly exploring ways to optimize every aspect of my life.
00:42:47.000 | And that just dominates every conversation I'm having. And it's just become my passion.
00:42:50.920 | What I spend my time on, on the nights, on the weekends, what I'm sharing with friends,
00:42:55.160 | and what I've become known for. I have friends that are now like, "You're my travel agent."
00:42:59.080 | And I actually got my travel agent license so that I could be actually a travel agent
00:43:03.160 | and book trips for them. The crazy thing that happened is, as we all know, there's the pandemic.
00:43:07.800 | And in some ways, I think people during the pandemic had more time to sit at home and do
00:43:12.680 | things like think about their finances because they weren't out doing other things. And I kept
00:43:17.480 | getting all these questions. And I was like, "Man, there's all these people asking me questions."
00:43:21.000 | And it's so unscalable to have one-off conversations. Before, it would be like
00:43:25.720 | a dinner party with 6 people. It felt a little better. And so Kevin from Milk, my old co-founder,
00:43:31.560 | ended up saying, "You got to start a podcast." And I thought, "Yeah, let's do it."
00:43:37.160 | I actually joined him on his show to talk about money hacks. At one point, he said,
00:43:41.800 | "Hey, tell me about your new podcast." And I was like, "Well, I haven't started it yet."
00:43:45.160 | And he's like, "Yeah, yeah. We'll cut this part out. You just need to record an answer
00:43:48.520 | to your new podcast and send it to me by Friday." And so I went home and I was like, "Okay. What's
00:43:52.440 | this podcast about? What's the theme? What's the trailer? What's the music?" And put it all together.
00:43:57.400 | And it's just blown past my wildest imagination because it turns out there are a lot of people
00:44:02.520 | out there that want to optimize their life. They want to do it while spending less money.
00:44:06.520 | They want to travel around the world and they want to do it in first class, if possible.
00:44:11.080 | So what are all the hacks to figure out ways to do that? To save money when you're shopping online
00:44:15.160 | in the holidays, to invest smarter, to use crypto to your advantage. All of this stuff is stuff we
00:44:21.960 | cover in the podcast. And now I spend a lot of my time, mostly on my nights and weekends, just
00:44:27.720 | digging into all the hacks, talking to the most interesting people I can.
00:44:31.480 | And that's my avenue for sharing all of these things with the world. We all start a newsletter.
00:44:36.600 | So if you don't like to listen... Well, I guess if you don't like to listen,
00:44:39.480 | I don't know why you're here right now. But we have a newsletter that compliments it pretty well.
00:44:43.160 | Now, can I turn it into a real business that finally fuels the burning desire to have
00:44:48.680 | something sustainable that I love? Maybe. I'm finally feeling like maybe I can start
00:44:52.840 | spending a little money. But keep in mind, for me, that's like I can finally order an
00:44:56.840 | extra appetizer. Spending a little bit more money for me is not as crazy as it is for some people,
00:45:01.960 | but I'm working on it. And I did a great episode with Ramit Sethi about this, where he's like,
00:45:07.400 | "Look, you got to learn how to live your own rich life. Everyone has a different version of it.
00:45:11.160 | You can find your version and you can create rules that allow you to have a little bit
00:45:15.480 | better relationship with money." We talked a lot about my girlfriend, my girlfriend,
00:45:19.080 | my girlfriend, right? And the fun story to throw back to our wedding was...
00:45:21.880 | I remember when we were getting married, I had seen a video from someone I knew,
00:45:27.720 | but didn't know that well, who had a lot of money's wedding. And they posted online. I was
00:45:31.320 | like, "Wow, that was a really impressive video." Like, "Gosh, if you could capture your wedding
00:45:35.560 | in that way, it would be wonderful." So at the end of the video, there's a little tag for who
00:45:39.560 | made it. I reach out and I'm like, "I would love to do a wedding video." I should have known that
00:45:43.480 | when they don't post their prices online, it means they're probably a lot. So ultimately, I'm like,
00:45:47.480 | "Oh, wow." It was over $10,000 for someone to make a wedding video, but I really wanted to do it.
00:45:52.920 | I got to talking to this woman who's now become a friend of mine. She was living in LA, but she was
00:45:57.320 | from Colorado. Amy, my wife was from Colorado. And we went to school there. We were just having
00:46:01.880 | good, fun conversations. And it came up that we were going on our honeymoon to the Seychelles.
00:46:08.200 | I thought for our honeymoon, let's go to the wildest, craziest place we could go.
00:46:11.000 | And let's, of course, do it on points. We ended up taking this honeymoon that cost...
00:46:16.120 | Just the flights alone were $20,000. The hotels were probably another $10,000, $15,000. We did
00:46:22.120 | all for free. If you use a credit card that earns two points, and those points are worth two cents,
00:46:27.000 | then you're effectively getting 4% cash back. We were getting a crazy value from being able to fly
00:46:33.240 | first class around the world. We ended up doing it in some of the best airlines with private
00:46:39.160 | suites and everything. But it was all points. I was telling this woman, Julie, who ran this
00:46:44.360 | production company about this trip we were taking. And she was like, "You're literally
00:46:49.080 | describing my dream vacation." And I was like, "What if we just send you on that vacation also,
00:46:55.320 | and you do the wedding for free?" And she was like, "I got to talk to my husband."
00:46:59.320 | And she came back. She was like, "We're in." Delta had this crazy promotion where if you send
00:47:04.360 | people miles, they would double them. They charge money to send people points, but not nearly enough
00:47:10.520 | that it mattered if they were going to double it. So we had all the points ready to book this flight.
00:47:14.840 | I transferred them from my account to my wife's account. And instantly, we had twice as many.
00:47:19.560 | For $1,000, we doubled the Delta miles that we needed to go on this trip. And I was like, "Boom,
00:47:24.520 | I just got our wedding video." I had this extra 240,000 points sitting here that we then used to
00:47:30.600 | send them. And they had an amazing time. And the trip probably would have cost them $20,000.
00:47:35.720 | So for them, they got a trip worth more than the wedding video. For me, I got a wedding video that
00:47:41.240 | we'll have for the rest of our lives for the $1,000 it cost to double my Delta miles.
00:47:46.280 | Those kinds of optimizations, those kinds of ways to enrich your life and upgrade your life
00:47:51.800 | are exactly what I live and thrive for and love sharing every week on Wednesdays at 2am.
00:47:59.480 | I just want to jump in and say thank you so much for listening this week.
00:48:12.520 | If you enjoyed hearing my story, or honestly, even if you didn't, please let me know.
00:48:16.680 | DM me or email me, chris@allthehacks.com. We'll be back with another interview next week.
00:48:22.760 | And if you enjoyed this style of interview, you can check out more from Founder Stories.
00:48:27.640 | See you next week.
00:48:36.360 | Transcribed by https://otter.ai
00:48:42.440 | [BLANK_AUDIO]