Latest / Trailblazers by Erica Wenger / Brian Kelly: How I Made $300k Per Month With Affiliate Marketing l Trailblazers Podcast Episode 52

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Brian Kelly: How I Made $300k Per Month With Affiliate Marketing l Trailblazers Podcast Episode 52 · Trailblazers by Erica Wenger

• 0:00
  [SPEAKER_00]: Today on the show, I am so excited to be joined by Brian Kelly.
• 0:04
  [SPEAKER_00]: Brian is the founder of the points guy.
• 0:06
  [SPEAKER_00]: The travel media platform he built from a personal blog into a genuine powerhouse.
• 0:10
  [SPEAKER_00]: One then out reaches more than 11 million visitors a month, with a full team of contributors acclaimed rankings and its own app.
• 0:16
  [SPEAKER_00]: David by the New York Times, the man who turned credit card points into an empire.
• 0:20
  [SPEAKER_00]: Brian turned a childhood obsession with miles and travel into an entire industry, and along the way inspired millions of people to make their own travel dreams real.
• 0:28
  [SPEAKER_00]: His expertise made him a regular on the country's top morning shows, good morning America, CBS mornings, and live with Kellyanne Mark among them, as well as CNBC, CNN, MSNBC, and Bloomberg.
• 0:38
  [SPEAKER_00]: He's been named Forbes number one travel influencer, landed on ad weeks young influencers, and travel and leisure's most notable people in travel, and is an out 100 honoree.
• 0:47
  [SPEAKER_00]: Ryan is also a firm believer that travel can be a global force for good.
• 0:50
  [SPEAKER_00]: He serves as a committee member for Rainbow Railroad, a global ambassador for Peace Jam, Co-chair of the Guvawi Peace Foundation Leadership Council, and a board member of the Hedgewick Martin Institute.
• 1:00
  [SPEAKER_00]: More recently, he's become a prolific angel investor, backing more than a dozen companies, including built.
• 1:05
  [SPEAKER_00]: The Red Rewords platform now valued in the billions.
• 1:07
  [SPEAKER_00]: Let's welcome Ryan.
• 1:11
  [SPEAKER_00]: What an epic buy-up.
• 1:13
  [SPEAKER_01]: It's, I always say it's never a dome woman.
• 1:16
  [SPEAKER_01]: That might be my autobiography title one day.
• 1:18
  [SPEAKER_00]: Yeah, it's like on the tombstone.
• 1:19
  [SPEAKER_00]: It was never a dome woman.
• 1:20
  [SPEAKER_01]: Truly though, every day is pretty fun, not gonna lie.
• 1:23
  [SPEAKER_00]: I love it, I love it.
• 1:24
  [SPEAKER_00]: Well, before we get into the interview, I like to start everything with an icebreaker, okay?
• 1:27
  [SPEAKER_00]: And it's not gonna be a softball.
• 1:29
  [SPEAKER_00]: It's gonna get right to the heart of it, okay?
• 1:30
  [SPEAKER_00]: We're going deep first.
• 1:31
  [SPEAKER_01]: Okay.
• 1:32
  [SPEAKER_00]: So when you look back on everything I just said, we think, you know, let's say 16 years ago, ish, you started the points guy.
• 1:38
  [SPEAKER_00]: What has been the hardest part of your journey?
• 1:40
  [SPEAKER_00]: It can be personal professional.
• 1:42
  [SPEAKER_01]: Professionally, the hardest thing I've ever done is write a book and have it be a New York Times bestseller.
• 1:47
  [SPEAKER_01]: That is a hustle to sell books these days.
• 1:51
  [SPEAKER_01]: There have been business luminaries that don't make the list and it wasn't just about making the list, but from editing,
• 2:01
  [SPEAKER_01]: a book and then bird it to the world then, you know, market it was super, super challenging, but I did it, but I'm not rushing to do it again anytime soon.
• 2:11
  [SPEAKER_00]: Yeah, I feel like once you've done it, you can kind of like ride that forever.
• 2:13
  [SPEAKER_01]: Yeah.
• 2:14
  [SPEAKER_00]: Like it's so hard to like 50 years when you're like, I am a New York Times best selling on this.
• 2:18
  [SPEAKER_00]: No one's going to got check when it happened.
• 2:20
  [SPEAKER_01]: Yeah, no one cares if you did it twice.
• 2:21
  [SPEAKER_00]: Yeah, that's true.
• 2:22
  [SPEAKER_01]: Yeah.
• 2:23
  [SPEAKER_00]: That's true.
• 2:23
  [SPEAKER_00]: It's kind of like building a giant business, like as long as you do once, you're always considered like a successful founder.
• 2:28
  [SPEAKER_01]: Yeah.
• 2:29
  [SPEAKER_00]: Yeah.
• 2:29
  [SPEAKER_00]: What was the hardest part of it?
• 2:30
  [SPEAKER_00]: Was it the writing?
• 2:31
  [SPEAKER_00]: Was it the, like, you know, running on your tour to try to get a bunch of books out?
• 2:36
  [SPEAKER_01]: Well, I love marketing.
• 2:37
  [SPEAKER_01]: So the marketing piece, once it was ready to go, I do tons and tons of media through the points guy have deep relationships.
• 2:43
  [SPEAKER_01]: So I had it.
• 2:44
  [SPEAKER_01]: lazy lineup of press and I love being on TV.
• 2:47
  [SPEAKER_01]: I love evangelizing especially for something that I believe strongly about like you know I've been doing the point sky for 15 years but so many people are still clueless with points.
• 2:55
  [SPEAKER_01]: I was like I need to write a book so people can leave me alone at dinner parties like read my book.
• 3:00
  [SPEAKER_01]: Don't ask me a question until you read my book.
• 3:02
  [SPEAKER_01]: Um, but writing it was a hard as part.
• 3:04
  [SPEAKER_01]: I have ADHD.
• 3:06
  [SPEAKER_01]: I am a perfectionist.
• 3:07
  [SPEAKER_01]: And that's the hardest thing where I wanted to go so deep on topics because I need to prove and drive it home, but you also have to be high level and keep a story going.
• 3:16
  [SPEAKER_01]: So trying to find that balance.
• 3:18
  [SPEAKER_01]: And I had so many stress stress dreams before launching it like no one's going to read it.
• 3:23
  [SPEAKER_01]: It's going to get paned.
• 3:24
  [SPEAKER_01]: It's going to get horrible reviews.
• 3:26
  [SPEAKER_01]: So that was.
• 3:28
  [SPEAKER_01]: You know, a really stressful time, many sleepless nights.
• 3:32
  [SPEAKER_01]: So I'm glad I did it though.
• 3:33
  [SPEAKER_00]: Yeah, you should be really proud.
• 3:34
  [SPEAKER_00]: I think the stress streams thing is not talked about enough.
• 3:37
  [SPEAKER_00]: Like that is when you know you're going something really challenging.
• 3:39
  [SPEAKER_00]: Yes.
• 3:40
  [SPEAKER_00]: I used to have dreams.
• 3:40
  [SPEAKER_00]: I was going to give a presentation where I would like blank, like blank in the middle of the thing.
• 3:45
  [SPEAKER_00]: That stuff, that's like what keeps you up.
• 3:46
  [SPEAKER_00]: Because you're not sleeping and you even fear running at you.
• 3:48
  [SPEAKER_01]: I have a dream, I'm not a singer.
• 3:49
  [SPEAKER_01]: That's like the one thing I hate.
• 3:50
  [SPEAKER_01]: I hate karaoke and I have a dream that I'm like, on American, I don't forget the lyrics.
• 3:54
  [SPEAKER_01]: And then I'm like, I'm not a dancer either.
• 3:56
  [SPEAKER_01]: I can't even dance to like, you know, but you're funny.
• 3:59
  [SPEAKER_00]: You could like crack Joe out.
• 4:00
  [SPEAKER_00]: Yeah, and you could be like, how close we forgot.
• 4:03
  [SPEAKER_01]: Or I'll just start singing Celine Dion.
• 4:04
  [SPEAKER_01]: Who's my favorite?
• 4:05
  [SPEAKER_00]: Me too.
• 4:06
  [SPEAKER_01]: I'm going to see her opening night of her return like for a residency in Paris.
• 4:12
  [SPEAKER_00]: Wait, I'm like, Celine Dion, but I didn't know she was coming back.
• 4:14
  [SPEAKER_01]: Yeah, she's coming back September 12.
• 4:16
  [SPEAKER_01]: She's doing a six week run.
• 4:17
  [SPEAKER_01]: So Celine Dion's a reason why I started the point sky.
• 4:20
  [SPEAKER_00]: Okay, so we got to get into all of that, but I thought she was sick.
• 4:22
  [SPEAKER_01]: She said, but she's back now.
• 4:24
  [SPEAKER_01]: So there's a piece of me that is nervous whether it's gonna happen.
• 4:28
  [SPEAKER_01]: She was just on the cover of Harper's Bazaar.
• 4:30
  [SPEAKER_01]: She's promoting it.
• 4:31
  [SPEAKER_01]: So I'm going night number one.
• 4:33
  [SPEAKER_01]: I actually did dream last night about it that I went to the concert and she was doing a sound check and they left me in.
• 4:38
  [SPEAKER_01]: And I experienced Celine Dion like dressed down doing a sound check.
• 4:41
  [SPEAKER_00]: The dream.
• 4:42
  [SPEAKER_01]: Yeah, but I was like far back and I needed to get closer and I didn't have tickets and I was stressed about getting kicked out.
• 4:48
  [SPEAKER_01]: That's my brain for you.
• 4:49
  [SPEAKER_00]: I love that, I love that you're uniquely you.
• 4:52
  [SPEAKER_00]: Just to let me know that she is the origin story of the points guy.
• 4:56
  [SPEAKER_01]: I've met her twice, so she, yeah, when I was starting the points guy, was at Morgan Stanley, and I started this blog, it started to take off, I knew I got so much joy from it, passion.
• 5:05
  [SPEAKER_01]: I've been doing points since the 90s, and, you know, I come from a middle class background.
• 5:11
  [SPEAKER_01]: I'm not in the entrepreneurship world, my parents are my dad's successful, my mom's
• 5:17
  [SPEAKER_01]: Mom and homemaker and also has a career but I didn't I was not raised to become like a business guru So when the when the points guy was taking off, I wanted to quit my job at Morgan Stanley and Everyone my mom's like what are you gonna do for benefits like everyone was kind of like sweetie the world doesn't need another travel blog You have to work in finance and I was less him
• 5:39
  [SPEAKER_01]: obsessed with Celine Dion.
• 5:40
  [SPEAKER_01]: I was listening to her song taking chances.
• 5:42
  [SPEAKER_01]: Through time square, I'm in my business casual, a tire, and I feel like such a worker be barking up seventh app, click, you know, my cackies, and I just was like, I don't, this isn't the life.
• 5:52
  [SPEAKER_01]: I've always known I was going to be rich and successful.
• 5:56
  [SPEAKER_01]: That has been a constant.
• 5:57
  [SPEAKER_01]: I knew I would do it, and listening to taking chances, it's all about taking chances, jumping off the ledge, not knowing
• 6:08
  [SPEAKER_01]: I talked to my boss.
• 6:09
  [SPEAKER_01]: I was like, I need to leave to do the points guy full time.
• 6:12
  [SPEAKER_01]: And I thought she'd be really mad.
• 6:13
  [SPEAKER_01]: She was like, good, you should.
• 6:14
  [SPEAKER_01]: And if it doesn't work out, come back.
• 6:16
  [SPEAKER_01]: And in my head, I had played out so many negative scenarios that she's gonna kick me out.
• 6:20
  [SPEAKER_01]: I'm gonna lose my benefits that day.
• 6:22
  [SPEAKER_01]: And it was just a lesson.
• 6:23
  [SPEAKER_01]: Selena was the, the nudge that I needed.
• 6:27
  [SPEAKER_01]: And when I met her, she was like, so was it a good decision?
• 6:30
  [SPEAKER_01]: And her brother reads my blog, who's like, her manager, who's like, so lean.
• 6:33
  [SPEAKER_01]: He gets to travel around the world in first class.
• 6:35
  [SPEAKER_01]: It was a good decision.
• 6:37
  [SPEAKER_00]: And also, he's meeting you now, like it's literally worked out.
• 6:39
  [SPEAKER_00]: If you're in a room with Celine Dion, it worked out.
• 6:41
  [SPEAKER_00]: Yes.
• 6:42
  [SPEAKER_00]: You know, it speaks for itself.
• 6:43
  [SPEAKER_01]: So I met her a second time several years later and she's like, so was it still a good decision?
• 6:48
  [SPEAKER_00]: She remembered.
• 6:49
  [SPEAKER_01]: And she, like, sees, I know, I'm six foot seven.
• 6:51
  [SPEAKER_01]: I'm front rotor concerts.
• 6:52
  [SPEAKER_01]: She, like, toys with me.
• 6:53
  [SPEAKER_01]: So that's like my, she's my, like, guiding force.
• 6:59
  [SPEAKER_00]: There's something in her music, too.
• 7:01
  [SPEAKER_00]: Like, I really feel this way.
• 7:02
  [SPEAKER_00]: I don't know what it is.
• 7:03
  [SPEAKER_00]: My sister and my mom did a dance at her wedding to because I loved you.
• 7:08
  [SPEAKER_00]: There's just something every song she sings.
• 7:11
  [SPEAKER_00]: You make a life decision.
• 7:12
  [SPEAKER_00]: It moves you so deeply.
• 7:15
  [SPEAKER_00]: It's like there's drugs in it or something.
• 7:16
  [SPEAKER_00]: It's so powerful.
• 7:17
  [SPEAKER_01]: It's like, yeah, if you let it, it's not just about the love.
• 7:21
  [SPEAKER_01]: People are just corny love songs, but there's actually like power behind it if you let it.
• 7:28
  [SPEAKER_01]: let it force you to quit your job and start a mini little empire.
• 7:32
  [SPEAKER_00]: One thing I've learned talking to GPs on the show and in my own experience as a GP, your back office is a signal.
• 7:38
  [SPEAKER_00]: How fast you close deals, how clean the LP experiences, how your K-1s land, and investors notice all of it.
• 7:44
  [SPEAKER_00]: The more buttoned up you are, the more likely they are to give you more money in the future.
• 7:48
  [SPEAKER_00]: That's why I want to talk about sidecar.
• 7:50
  [SPEAKER_00]: Sidecar is the SPV platform built for fund managers who want institutional quality execution without hiring a full back office team.
• 7:58
  [SPEAKER_00]: They'll review your deal with an hours,
• 8:02
  [SPEAKER_00]: and give you transparent pricing up front.
• 8:04
  [SPEAKER_00]: No platform carry.
• 8:05
  [SPEAKER_00]: Also, your LP relationship state private, which is super important.
• 8:08
  [SPEAKER_00]: It is not a marketplace.
• 8:10
  [SPEAKER_00]: If you're running a professional fund, your infrastructure should look like it.
• 8:13
  [SPEAKER_00]: Sidecar makes that possible without the overhead.
• 8:15
  [SPEAKER_00]: Check them out at sidecar.io slash partners slash trailblazers.
• 8:19
  [SPEAKER_00]: So let's go back to the beginning.
• 8:20
  [SPEAKER_00]: You quit the job.
• 8:22
  [SPEAKER_00]: You start the points.
• 8:23
  [SPEAKER_00]: Guy, this is 16 years ago, which is insane.
• 8:25
  [SPEAKER_00]: Talk to me about those first couple years.
• 8:27
  [SPEAKER_00]: I know they were a while.
• 8:28
  [SPEAKER_00]: You were growing like fast and there was a sale.
• 8:30
  [SPEAKER_00]: happened really early on in your journey, which is, by the way, I mean, unique and rare as it is an unsatement.
• 8:36
  [SPEAKER_00]: Talk to me about that whole story.
• 8:37
  [SPEAKER_01]: The quick timeline, so I start the blog and actually the points guy wasn't even content at first.
• 8:41
  [SPEAKER_01]: It was, I was a travel agency.
• 8:43
  [SPEAKER_01]: So I was helping everyone I know book flights and one day my exploiter was like, you should charge people for this because you're saving them thousands of dollars like they'd be glad to pay you.
• 8:52
  [SPEAKER_01]: So I started the points guy as you would submit a form on my website, tell me what points you had and I would charge you $50 to tick it.
• 8:59
  [SPEAKER_01]: So it's just a side hustle, you know, I would come home from Morgan Stanley, I was in HR recruiting, so I'm not making a lot of money.
• 9:05
  [SPEAKER_01]: So, you know, a couple hundred bucks, a thousand bucks a month on the side was like, okay, nice little,
• 9:12
  [SPEAKER_01]: You know, so I gig and I then started a friend of mine was a WordPress developer.
• 9:18
  [SPEAKER_01]: So he's like, you have to blog, you have to blog and so he set me up with the WordPress site in June of 2010.
• 9:25
  [SPEAKER_00]: And like the landscape of like blogging at this time.
• 9:26
  [SPEAKER_01]: So blogging at this time, there had been blogs for at the 2000s, but I think 2010 was when fashion bloggers started getting invites to fashion shows.
• 9:34
  [SPEAKER_01]: Like it was really the right time in place.
• 9:36
  [SPEAKER_01]: This is pre Instagram.
• 9:38
  [SPEAKER_01]: Instagram wasn't really until 2012.
• 9:40
  [SPEAKER_01]: I think is when I joined.
• 9:41
  [SPEAKER_01]: Twitter was around Facebook, was really growing, and there was a community called Flyer Talk, which was, you know, pre-read it was not around.
• 9:50
  [SPEAKER_01]: But Flyer Talk was the Reddit for frequent travelers.
• 9:52
  [SPEAKER_01]: I had been in that community since 2004.
• 9:55
  [SPEAKER_01]: So I, but that community was so unorganized.
• 9:59
  [SPEAKER_01]: Like, Reddit's pretty organized today and pretty easy to, but Flyer Talk was like coded.
• 10:03
  [SPEAKER_01]: People gate kept.
• 10:05
  [SPEAKER_01]: All the frequent flyer secrets.
• 10:06
  [SPEAKER_01]: So I was like,
• 10:07
  [SPEAKER_01]: Well, I can translate to the masses, which they, of course, hated, but I saw business opportunity, you know, people working in finance and consulting.
• 10:16
  [SPEAKER_01]: There was a huge group of affluent consumers that were still confused and too busy to take the years of time like I had.
• 10:23
  [SPEAKER_01]: So let me translate that.
• 10:24
  [SPEAKER_01]: I made no money, you know, Google ad cents at the time.
• 10:27
  [SPEAKER_01]: I was making $20 a month.
• 10:29
  [SPEAKER_01]: But the turning point for me was in 2011, I got into affiliate marketing.
• 10:33
  [SPEAKER_01]: So unbeknownst to me, I was blogging on a gold mine because my audience, though not huge, was rich.
• 10:40
  [SPEAKER_01]: Good credit scores.
• 10:41
  [SPEAKER_01]: The Henry's high earning, not rich yet.
• 10:44
  [SPEAKER_01]: Millennials at the banks were obsessed with getting.
• 10:46
  [SPEAKER_01]: We're outside of the financial crisis.
• 10:49
  [SPEAKER_01]: They were all about getting the younger card holders that would become their bread and butter.
• 10:56
  [SPEAKER_01]: So I write time, write place, write audience.
• 10:58
  [SPEAKER_01]: And in affiliate marketing, my first month was $5,000, and then in April of 2010, I learned that leveraging press, so I had a New York Times article come out, which, by the way, was in my spam inbox for two months.
• 11:13
  [SPEAKER_01]: Seth Kugel of the New York Times, who was a frugal travel editor, had email me.
• 11:16
  [SPEAKER_01]: So any entrepreneurs out there, check your spam.
• 11:18
  [SPEAKER_01]: Inbox periodically, because that email changed my life.
• 11:21
  [SPEAKER_01]: He ended up writing a story, because I changed his whole perspective on points.
• 11:25
  [SPEAKER_01]: in April of 2010 and that link back and it wasn't in print and I felt like such a failure because my parents were like, oh, sweetie, you didn't make it in the print.
• 11:33
  [SPEAKER_01]: But the best thing they gave me was a digital link back from the New York Times to the point sky.
• 11:38
  [SPEAKER_01]: In 2011, that was what Google, that was huge signal to SEO.
• 11:43
  [SPEAKER_01]: So my site from that point on rocketed and there was a affiliate offer for a hundred thousand points in a British
• 11:51
  [SPEAKER_01]: that the day the New York Times article came and just sent thousands of people, so I made 120 grand that day.
• 11:59
  [SPEAKER_01]: And so while Celine definitely helped push me over the edge, like I felt this tidal wave like that this could be a real real business if I actually did it full time and wasn't doing it on the sidelines of my 70,000-dollar year, HR job at a bank.
• 12:14
  [SPEAKER_00]: Yeah, it's unbelievable.
• 12:16
  [SPEAKER_01]: So yeah, so I made a million dollars in six months and then an April of 2011.
• 12:21
  [SPEAKER_01]: So just about a year of revenue, I think I made $3 million in a year.
• 12:26
  [SPEAKER_00]: Not too bad.
• 12:27
  [SPEAKER_00]: A little bit of that said okay.
• 12:28
  [SPEAKER_01]: Pretty much I had known investors.
• 12:31
  [SPEAKER_01]: $10 domain I bought myself was doing myself.
• 12:33
  [SPEAKER_01]: I had a couple of part time employees in the beginning.
• 12:36
  [SPEAKER_01]: No equity.
• 12:37
  [SPEAKER_01]: And so bank rate, this publicly traded company.
• 12:40
  [SPEAKER_01]: friend of a friend knew the CEO I went in to meet with him zero plan no deck no business plan I kind of just went in to meet him and that night he sent me an email like I want to buy your blog And I'm like what are they gonna buy it for?
• 12:52
  [SPEAKER_01]: It's been one year and also I'm making 300 grand a month cash as a 27-year-old Judging around the world.
• 12:58
  [SPEAKER_01]: I'm like I don't want to go back into corporate But I and I didn't have a team of bankers because I wasn't for sale, but I had a
• 13:06
  [SPEAKER_01]: a great tax attorney at Grimberg Trog, and he was my advisor.
• 13:09
  [SPEAKER_01]: So I one-on-one negotiated the sale over six weeks.
• 13:13
  [SPEAKER_01]: It was a crazy six weeks of my life, but I ended up with $28 million, three and a half year earnout.
• 13:19
  [SPEAKER_01]: And I just thought I would be stupid to not take, I think it was eight million cash on closing day.
• 13:24
  [SPEAKER_01]: It's a 28-year-old.
• 13:26
  [SPEAKER_01]: Then I was like, I'll always be able to, you know, I have enough money now that no matter what happens, I can, you know, I know I have the skills to do something.
• 13:33
  [SPEAKER_01]: So,
• 13:34
  [SPEAKER_01]: But I'm still here all these years later, which is even crazier and in 2017, Bank Creek got bought by a company called Red Ventures.
• 13:42
  [SPEAKER_01]: Red Ventures is still owns the point sky.
• 13:46
  [SPEAKER_01]: I ran it till 2020 and in 2020 I had.
• 13:52
  [SPEAKER_01]: I would just say a burnout, you know, being the face of the brand, going on TV, being behind the scenes, working with the parent company, flying back and forth to Charlotte, the performance, you know, with then 120 employees, like I never started the point sky to be in media, uh, executive managing creatives and the business side, so I definitely I had a burnout moment where I was like, is this, it's been 10 years, should I just leave?
• 14:18
  [SPEAKER_01]: But I love what we do.
• 14:19
  [SPEAKER_01]: I love, I mean, my job is the best job in the world.
• 14:21
  [SPEAKER_01]: I walked down the street and people, you know, some province sound this past week.
• 14:25
  [SPEAKER_01]: People come up to me and just say, you changed my life.
• 14:27
  [SPEAKER_01]: I love you.
• 14:28
  [SPEAKER_01]: I got to visit my sick mother before she passed because of points.
• 14:32
  [SPEAKER_01]: And I was doing this.
• 14:33
  [SPEAKER_01]: Like, so that is what drives me.
• 14:36
  [SPEAKER_01]: I didn't want to walk away from that.
• 14:37
  [SPEAKER_01]: Because the mission of the points guy is still deeply, you know, moved by.
• 14:42
  [SPEAKER_01]: And yeah, with red ventures, they said, good, like stop managing, there are people that can do that.
• 14:46
  [SPEAKER_01]: You're special.
• 14:47
  [SPEAKER_01]: Do what you do best.
• 14:48
  [SPEAKER_01]: Not everyone can go on with Gayle King and shoot the shit and also get our brand in front of millions of people consistently.
• 14:56
  [SPEAKER_01]: So that was a really cool moment.
• 14:57
  [SPEAKER_01]: Once again, similar to leaving Morgan Stanley, where in my head I was like, well, if I tell them I can't do this, then it's going to be leave, get out.
• 15:04
  [SPEAKER_01]: But that was when I knew, I mean, I knew it always I've been an asset to the company.
• 15:09
  [SPEAKER_01]: And so yeah, in 2020, I switched into just being the full-time, evangelist spokesperson, which is what I love doing.
• 15:16
  [SPEAKER_01]: I met that same exact time, pandemic hit.
• 15:18
  [SPEAKER_01]: I'm not traveling.
• 15:20
  [SPEAKER_01]: I also realized I had more time to focus on now investing my wealth.
• 15:25
  [SPEAKER_01]: And I had a couple interesting people knock on my door, including Uncle Jane, the CEO and founder of built.
• 15:32
  [SPEAKER_01]: And I thought, well, if this isn't an opportunity to take some of this time now that I have not
• 15:38
  [SPEAKER_01]: managing this company.
• 15:40
  [SPEAKER_01]: So I really started to angel investing at that point and throughout the pandemic and you know, building my biggest one I got in on that is a safe note.
• 15:47
  [SPEAKER_01]: I got in before it was even called built as a concept.
• 15:51
  [SPEAKER_01]: Put a bunch of money into it too.
• 15:53
  [SPEAKER_01]: In addition to getting a lot of advisory shares.
• 15:55
  [SPEAKER_01]: So yeah, built's been life changing.
• 15:57
  [SPEAKER_00]: that's so epic.
• 15:59
  [SPEAKER_00]: Let's maybe touch on.
• 16:00
  [SPEAKER_00]: I want to jump back a bit and touch a little bit on affiliate revenues.
• 16:02
  [SPEAKER_00]: People understand how you've got here.
• 16:04
  [SPEAKER_00]: Because when you say you go from zero quitting the job to $20 million sale, $300K cash a month, these numbers are insane to people.
• 16:13
  [SPEAKER_00]: Just quickly tell us, how does that work?
• 16:15
  [SPEAKER_00]: So there's a British airways flight.
• 16:17
  [SPEAKER_00]: It's used that example.
• 16:18
  [SPEAKER_00]: You open up a credit card.
• 16:19
  [SPEAKER_00]: You get 100,000 points.
• 16:21
  [SPEAKER_00]: How are you making money on that?
• 16:22
  [SPEAKER_00]: Just tell everyone the mechanics there.
• 16:23
  [SPEAKER_01]: The mechanics are this.
• 16:24
  [SPEAKER_01]: So a lot of internet advertising is per view.
• 16:28
  [SPEAKER_01]: You need to have millions of views, and they're paying you pennies on the dollar.
• 16:31
  [SPEAKER_01]: But that's a big publisher as they sell added inventory.
• 16:35
  [SPEAKER_01]: And whether you click and buy something or not, they're still getting paid.
• 16:37
  [SPEAKER_01]: Well, I didn't have the traffic for that.
• 16:39
  [SPEAKER_01]: But I had a really engaged audience
• 16:43
  [SPEAKER_01]: So when I recommend an AMX Platinum card, if you get an AMX Platinum card, I'm just going to say back in 2011, it was maybe $400.
• 16:50
  [SPEAKER_01]: So I would get paid zero if you clicked a link and didn't get the card, but you read my review, I got $0, but if you clicked it, we're like, oh, I want to go to the lounge.
• 16:59
  [SPEAKER_01]: I didn't realize I could transfer to Air France for 60,000 points, which is the amount of the sign-up bonus.
• 17:04
  [SPEAKER_01]: So I was able to market credit cards in a way, and say, this is how I use it, and I'm six foot seven,
• 17:12
  [SPEAKER_01]: comfortably around the world for free on points from this credit card.
• 17:15
  [SPEAKER_01]: By the any of the article, you're like, I'm going to get this.
• 17:17
  [SPEAKER_01]: I get it now.
• 17:18
  [SPEAKER_01]: Instead of just seeing a glossy ad in the Wall Street Journal, I think the credit card companies were realizing that bloggers could...
• 17:25
  [SPEAKER_01]: get their message across way better.
• 17:27
  [SPEAKER_01]: So I would get paid, say, $400.
• 17:30
  [SPEAKER_01]: So in the beginning, when my audience was small, that was 5,000 in the first month.
• 17:34
  [SPEAKER_01]: But when I started to realize, using my talents to speak to media, to drive huge new audiences to the site.
• 17:42
  [SPEAKER_01]: And at the same time, Google was realizing all these signals.
• 17:45
  [SPEAKER_01]: After New York Times, I went on CNN.
• 17:47
  [SPEAKER_01]: I went to media training.
• 17:49
  [SPEAKER_01]: that's a huge tip I have for founders.
• 17:51
  [SPEAKER_01]: Go to media training.
• 17:52
  [SPEAKER_01]: Even if you don't want to be the main spokesman for your company learning how to speak to media and being comfortable in front of the camera is a huge
• 18:03
  [SPEAKER_01]: A key message I have to founders is get media trained.
• 18:06
  [SPEAKER_01]: Spend two days, go to professionals.
• 18:08
  [SPEAKER_01]: They will put you in different settings, like a radio interview, a TV interview.
• 18:12
  [SPEAKER_00]: And Chile is a podcast.
• 18:13
  [SPEAKER_01]: Yeah, yeah, podcast because you, I got millions of dollars worth of free advertising.
• 18:20
  [SPEAKER_01]: and continue to do so by leveraging media because when media you get on the media it's not just you talking about your company you need to be entertaining you need to give the audience and you need to be a good guess that they know if they have you back on you're not going to be a waste of time and you always have to give nuggets to the audience while speaking to the host so it's it's challenging it is hard it is a skill you need to learn but I learned that early on and that was
• 18:43
  [SPEAKER_01]: a game changer because not only was I getting new audiences for every article, every TV show, the brand awareness, which then also helped me go into MX and Chase, Brian is now the media darling, right?
• 18:55
  [SPEAKER_01]: So when the there's a whole strategy behind it, when you become a media star, social media star, your value goes up.
• 19:03
  [SPEAKER_01]: So when budgets get cut and this happened all the time and still happens and they need to get rid of publishers.
• 19:09
  [SPEAKER_01]: They're going to think twice about the point sky because not only am I driving you really high quality customers, but I'm a voice media.
• 19:16
  [SPEAKER_01]: And often in the media, I'm asked, what are the best credit cards right now?
• 19:19
  [SPEAKER_01]: So being powerful in media has a multitude of benefits to your business and learning how to do that, I think is a skill that will pay for itself many times over.
• 19:29
  [SPEAKER_00]: totally.
• 19:30
  [SPEAKER_00]: And I think especially because founder-led brands are becoming so much more important.
• 19:33
  [SPEAKER_00]: Like even if you don't even want to be a creator, just like knowing how to lead your company and storytelling properly.
• 19:38
  [SPEAKER_00]: What does it even mean to be media-trained?
• 19:40
  [SPEAKER_00]: Like do you type in LinkedIn, media-trainer?
• 19:42
  [SPEAKER_00]: Yeah, how do you find someone?
• 19:43
  [SPEAKER_01]: Yeah, there are professional media trainers out there, usually former journalists, and they will put you through bootcamp.
• 19:50
  [SPEAKER_01]: I went in Chicago for two days, did fake, and you have to watch yourself back.
• 19:54
  [SPEAKER_01]: So they'll tell you your mannerisms,
• 19:59
  [SPEAKER_01]: It's very no one likes watching themselves, but it is the best because professionals will give you tips.
• 20:05
  [SPEAKER_01]: Most importantly, I think when you start going on in media, you're worried about something bad happening or being asked to question you don't know the answer to.
• 20:12
  [SPEAKER_01]: they'll teach you the art of bridging.
• 20:15
  [SPEAKER_01]: So, no matter what your ass, you know how to always bring it back to something that you want.
• 20:21
  [SPEAKER_01]: And you also have to get your points across.
• 20:23
  [SPEAKER_01]: You have to be used at time to your advantage as well, but not by being overly salesy because then people check out.
• 20:29
  [SPEAKER_01]: It's a fine balance.
• 20:30
  [SPEAKER_01]: So media training, go to official media training, spend, it's not that expensive, but spend the time and push yourself.
• 20:40
  [SPEAKER_00]: love that.
• 20:40
  [SPEAKER_00]: Let's talk about the messy middle of building an audience.
• 20:43
  [SPEAKER_00]: You've got your newsletter and one tool, your podcast and another, your website hosted somewhere else entirely and your community is scattered across multiple apps.
• 20:51
  [SPEAKER_00]: You have to pay for four different subscriptions and then they still take a cut of your earnings.
• 20:55
  [SPEAKER_00]: Set Sound familiar?
• 20:56
  [SPEAKER_00]: Behive is just fix this with their latest update.
• 20:59
  [SPEAKER_00]: It's one platform where your newsletter, your podcast, your website, your paid subscriptions, and now your community can all live together.
• 21:07
  [SPEAKER_00]: Everything talks to each other because it's finally under one roof.
• 21:10
  [SPEAKER_00]: And here's the part creators like myself love most.
• 21:12
  [SPEAKER_00]: when you earn on B-Hive, you actually get to keep all of it.
• 21:15
  [SPEAKER_00]: So there's zero percent taking from your subscriptions, zero percent from your digital products, and publishers on the platform have actually made tens of millions in revenue and kept every single cent.
• 21:24
  [SPEAKER_00]: So if you're tired of stitching tools together and ready to actually own your audience, go to B-Hive.com and use the code Trailblazers30 for 30% off your first three months.
• 21:33
  [SPEAKER_00]: That's B-Hive, B-E-E-H-I-I-V.com code Trailblazers30.
• 21:38
  [SPEAKER_00]: So I have a confession.
• 21:39
  [SPEAKER_00]: I used to be a compulsive note-taker.
• 21:41
  [SPEAKER_00]: Every single meeting, I'd be half listening and half scribbling and still leaving with gaps on next steps, details that were shared and more, but Granola completely changed that for me.
• 21:50
  [SPEAKER_00]: It's an AI-powered note-pad for meetings and it's expected to every single call on my calendar.
• 21:54
  [SPEAKER_00]: Before each call, it shows me a well-researched brief, so I knew who I'm meeting with and the full context going in.
• 21:59
  [SPEAKER_00]: During the call, I jot down whatever stands out, maybe it's a key word or a decision I make, and granola handles the rest.
• 22:05
  [SPEAKER_00]: It'll transcribe in the background on the call and then turns my rough notes into clean, structured takeaways, the second we hang up.
• 22:12
  [SPEAKER_00]: There's also no bots joining calls.
• 22:14
  [SPEAKER_00]: It just works in the background.
• 22:16
  [SPEAKER_00]: I use granola for several things.
• 22:17
  [SPEAKER_00]: If I finish a meeting with the potential investor in my fund, I'll ask granola, what could I have done better to get my point across?
• 22:23
  [SPEAKER_00]: If I'm meeting with a founder I like, I'll ask granola to point out any major green flags or maybe red flags I may not have already caught.
• 22:29
  [SPEAKER_00]: For people with a lot of deem meetings and decisions that require endless context, granola is a game-tanger.
• 22:34
  [SPEAKER_00]: Actually, we're running granola on today's episode so you can read the full show notes at granola.ai-slash trailblazers.
• 22:40
  [SPEAKER_00]: New users get three months completely free that's granola.ai-slash trailblazers.
• 22:45
  [SPEAKER_00]: So jumping back to the affiliate revenue stuff, because I think this is in particular really interesting.
• 22:50
  [SPEAKER_00]: You really had a gold mine.
• 22:51
  [SPEAKER_00]: You had a gold mine.
• 22:52
  [SPEAKER_00]: You crushed it with the media, so you went up an SEO.
• 22:55
  [SPEAKER_00]: You made so much money, you get the sale.
• 22:56
  [SPEAKER_00]: AI's changing a lot of things.
• 22:58
  [SPEAKER_00]: AI's changing where we get our recommendations.
• 23:01
  [SPEAKER_00]: It's changing SEO as many as I call it, A.E.O.
• 23:03
  [SPEAKER_00]: now, right?
• 23:05
  [SPEAKER_00]: How are you thinking about affiliate revenue a little bit differently now?
• 23:08
  [SPEAKER_00]: And I'd love to talk about how the business has evolved in terms of the business model, since,
• 23:12
  [SPEAKER_00]: you know, that crazy 2011 year, 2012 year, all the way to today.
• 23:16
  [SPEAKER_01]: Yeah, so the business models changing, you have to in media change.
• 23:19
  [SPEAKER_01]: And by the way, when I got into affiliate marketing, no one else was really doing it in publishing.
• 23:23
  [SPEAKER_01]: And I felt felt like it was almost scamming away and like will I be respected?
• 23:28
  [SPEAKER_01]: Can I still go on the today's show if I have a website where I'm making money?
• 23:32
  [SPEAKER_01]: But eventually when I ended up happening is all of the major
• 23:36
  [SPEAKER_01]: You know, Vogue, everyone has affiliate marketing because that's where you make money with your engaged audience So but over the years we want, you know, affiliate is a huge part of our revenue because, you know, once you rank is the MX Platinum card worth it And you have that top one or even top six spot that's just constant money that's coming in and you need to continue updating that post
• 23:58
  [SPEAKER_01]: Um, but yeah, with AI now, certainly everything's changing, but there are ways, you know, most AI platforms pulling the points guy, but we're not getting paid on the click necessarily, so it's about working with advertisers saying, look, our content is going to fill AI results.
• 24:14
  [SPEAKER_01]: We're not going to get paid on it.
• 24:15
  [SPEAKER_01]: So let's think about a longer term strategy.
• 24:17
  [SPEAKER_01]: Let's think about a holistic way of getting paid, not just on acquisition.
• 24:22
  [SPEAKER_01]: Because by the way, you also need to retain all these cardholders.
• 24:25
  [SPEAKER_01]: And so back in the day,
• 24:26
  [SPEAKER_01]: The card issue was really just focused on acquisition, getting as many new card holders as possible.
• 24:31
  [SPEAKER_01]: But now what we've seen in my book, how to win a travel, I call this the Platinum Age of Travel.
• 24:35
  [SPEAKER_01]: There's so much competition, consumers are, you know, can go from one issue or to another, the issuers now need to retain their customers.
• 24:43
  [SPEAKER_01]: So we're working with issuers on retention content, on brand partnerships.
• 24:48
  [SPEAKER_01]: We create, we have a content studio where we can work with not just a credit card companies, but travel.
• 24:54
  [SPEAKER_01]: We have, I'm not the only talent at the company.
• 24:55
  [SPEAKER_01]: We have about 15 other spokespeople, content creators.
• 25:00
  [SPEAKER_01]: We can help brands shape their messaging, whether it's through AI results, search is still important.
• 25:06
  [SPEAKER_01]: YouTube is still extremely important.
• 25:08
  [SPEAKER_01]: So the landscape is shifting, but our value is not just from a blog post.
• 25:14
  [SPEAKER_01]: And that's why over the years, we expanded beyond just a blog into,
• 25:20
  [SPEAKER_01]: technology and to content partnerships across social media.
• 25:24
  [SPEAKER_00]: So yeah, well, that's how you've stayed relevant.
• 25:26
  [SPEAKER_00]: I mean, it's very hard to build a media business 16 years ago.
• 25:29
  [SPEAKER_00]: And still be even more relevant actually today, which is super exciting.
• 25:33
  [SPEAKER_01]: I can't speak numbers, but it's been very profitable always.
• 25:36
  [SPEAKER_01]: Even in the deepest arc of days of the recession, we may be lost money a couple months, but like immediately, you know, year over year, I mean, it's been a very profitable company,
• 25:50
  [SPEAKER_01]: evolving and we have a new CEO, Liza Lansman, who is a seasoned executive and financial services, she helped seljet.com, she's got a big vision, she's recruiting top tier talent.
• 26:03
  [SPEAKER_01]: So it's fun to be a part of a team that we have experts across the board and yeah, you've got to just like a shark, you've got to keep moving or you die.
• 26:14
  [SPEAKER_00]: Um, I love that you brought up Liza.
• 26:15
  [SPEAKER_00]: So I know Liza.
• 26:17
  [SPEAKER_00]: She is the best and fun fact.
• 26:19
  [SPEAKER_00]: She's got a venture background.
• 26:20
  [SPEAKER_00]: Yeah.
• 26:20
  [SPEAKER_00]: Right.
• 26:21
  [SPEAKER_00]: Shout out to NEA.
• 26:23
  [SPEAKER_00]: How did you convince Liza to join you?
• 26:24
  [SPEAKER_00]: I will tell you.
• 26:25
  [SPEAKER_00]: I saw her background.
• 26:26
  [SPEAKER_00]: Someone introduced us and I see this just killer background venture.
• 26:31
  [SPEAKER_00]: And then all of a sudden I see CEO of the points guy.
• 26:33
  [SPEAKER_00]: New job for her.
• 26:35
  [SPEAKER_00]: And I'm thinking,
• 26:36
  [SPEAKER_00]: Good for Brian, good for the team, but that is a good get.
• 26:39
  [SPEAKER_00]: So tell me how you got her and why you wanted that profile.
• 26:42
  [SPEAKER_01]: You know, and we interviewed tons and tons of people.
• 26:46
  [SPEAKER_01]: And I really pushed our, our parent company red ventures.
• 26:49
  [SPEAKER_01]: A lot, we had a lot of internal candidates coming to run the points guy.
• 26:52
  [SPEAKER_01]: And they had their own marketing expertise, but I really pushed our CEO, Rick Elias.
• 26:57
  [SPEAKER_01]: We've got to get an external candidate.
• 26:59
  [SPEAKER_01]: We can't just keep pulling from our internal playbook, which has served Red Ventures very well, but being where you need brand and in the Red Ventures portfolio, we also, you know, we own lonely planet, bank rate and a bunch of other sites, but the points guy has, it's a brand, it is a household name that, it just deserves a higher caliber leader.
• 27:21
  [SPEAKER_01]: So,
• 27:24
  [SPEAKER_01]: You know, we interviewed tons and tons of people and we, when we found Liza, you know, she met everyone there and I said to her, we're gonna have fun.
• 27:32
  [SPEAKER_01]: I mean, she is a growth executive.
• 27:35
  [SPEAKER_01]: We're growing and but we needed more external people and she has an incredible network.
• 27:40
  [SPEAKER_01]: So I kind of laid out like, I'm here to work.
• 27:43
  [SPEAKER_01]: I keep signing deals to stay on with the points guide because they let me do what I love.
• 27:48
  [SPEAKER_01]: I can also, you know, do my personal investing
• 27:51
  [SPEAKER_01]: So to me, it's the best of all world because I'm more valuable to my and best, you know, the companies that I invest in, being a part of the points guys.
• 27:58
  [SPEAKER_01]: So I said, I'm on, I'm going to stay, let's build this and do it together.
• 28:02
  [SPEAKER_01]: And I think, not the end of the day, just you need to like the people you work with.
• 28:06
  [SPEAKER_00]: And I'm sure they're grateful to that you are so self-aware of what you're good and about it.
• 28:11
  [SPEAKER_00]: Like, I think that's not much of it.
• 28:12
  [SPEAKER_01]: There's no competition.
• 28:15
  [SPEAKER_01]: I do not want to run this company.
• 28:17
  [SPEAKER_01]: I want to win.
• 28:18
  [SPEAKER_01]: I'm a winner.
• 28:19
  [SPEAKER_01]: And I want to work with smart people who know
• 28:23
  [SPEAKER_01]: where the blind spots are in our organization, and she's immediately pulled in a bunch of people.
• 28:28
  [SPEAKER_01]: She's worked within the past and product marketing.
• 28:31
  [SPEAKER_01]: We have a new CMO, Jackie Stern, who's fabulous.
• 28:33
  [SPEAKER_01]: So yeah, it's a powerful team.
• 28:36
  [SPEAKER_01]: Times are shifting, it is challenging, but when you have a good executive team, anything is possible.
• 28:41
  [SPEAKER_01]: So I'm excited for the next chapter of the points guy.
• 28:44
  [SPEAKER_00]: And you've built a great foundation, you know.
• 28:46
  [SPEAKER_00]: We can give credit where credit's still.
• 28:47
  [SPEAKER_01]: Yeah.
• 28:48
  [SPEAKER_00]: I love it.
• 28:49
  [SPEAKER_00]: So let's talk about your personal investing.
• 28:50
  [SPEAKER_00]: Because this is something that I obviously spend a lot of my time thinking about.
• 28:53
  [SPEAKER_00]: And I want to get into the weeds with you and how you think about it.
• 28:55
  [SPEAKER_00]: So your COVID hits and you're like, OK, I get this built opportunity.
• 29:00
  [SPEAKER_00]: But I want to do more investing even beyond that.
• 29:02
  [SPEAKER_00]: What is the thesis?
• 29:03
  [SPEAKER_00]: What was like the rationale?
• 29:04
  [SPEAKER_00]: Was it I have this bucket of capital?
• 29:07
  [SPEAKER_00]: And I want to deploy it.
• 29:08
  [SPEAKER_00]: Was it I have these opportunities?
• 29:09
  [SPEAKER_00]: And I want to find the capital.
• 29:10
  [SPEAKER_00]: Tell me how it came about.
• 29:11
  [SPEAKER_01]: So the first investment I did actually was the morning brew.
• 29:14
  [SPEAKER_01]: So, yeah, awesome.
• 29:16
  [SPEAKER_01]: Alex, yeah.
• 29:16
  [SPEAKER_01]: Awesome.
• 29:16
  [SPEAKER_01]: And Alex DM me for, I think, a year, and I was so busy being CEO of the points guy, you know, just focused on growing my business.
• 29:25
  [SPEAKER_01]: I'm making a lot of money there, and I'm doing some brand deals on the side.
• 29:28
  [SPEAKER_01]: So I'm like, I want cash.
• 29:29
  [SPEAKER_01]: I don't want equity in this random startup.
• 29:31
  [SPEAKER_01]: But finally, I think I put $30,000 in, but what I loved about it, I advised them.
• 29:36
  [SPEAKER_01]: Me and I didn't even know to ask for advisory shares, and then even as what I learned a lot
• 29:43
  [SPEAKER_01]: And then I wasn't even able to put more money in because I didn't negotiate those terms.
• 29:47
  [SPEAKER_01]: I was being too nice about it.
• 29:48
  [SPEAKER_01]: And I was like, let me just knowing what I know now and the value I can bring you in the doors.
• 29:52
  [SPEAKER_01]: I'll open you and how I super charge your business like you're gonna let me.
• 29:56
  [SPEAKER_01]: put more in when that time comes and you're also going to give me advisory because my name being attached to this and my instant network will bring immediate value and you're just going to share a little bit of very so I learned you know so I ten X I got a 300 k pay out I think three years after my investment I'm like a wait a minute this is really good
• 30:17
  [SPEAKER_01]: And I didn't even negotiate for the best term.
• 30:19
  [SPEAKER_01]: So when built came around, I negotiated for those terms, which is a blessing, because built has been growing, you know, 11 billion in less than five years, and I think we'll go way higher than that.
• 30:31
  [SPEAKER_01]: I'm extraordinarily bullish on what the team is building there.
• 30:34
  [SPEAKER_01]: Um, and then after Bill, I mean, I, I'm so lucky I have an amazing deal flow in flowing.
• 30:39
  [SPEAKER_01]: So, especially after Billet and I really, I, because I believed in Billet, and Ankwer has said publicly, like, Bill wouldn't be what it is today without me fully, fully throttle endorsing that, bringing the right influencers on board and getting media aware of just how incredible it is.
• 30:56
  [SPEAKER_01]: And once I really help,
• 30:58
  [SPEAKER_01]: was one of the people who helped built really take off and very fast, then I think a lot of other companies and I were like, wow, an encore will tell anyone.
• 31:06
  [SPEAKER_01]: Like, I don't do anything have fast.
• 31:08
  [SPEAKER_01]: I'm here to win.
• 31:09
  [SPEAKER_01]: I wanna, you know, I'm never gonna get advisory and then go at my A, that is just not who I am as a person.
• 31:15
  [SPEAKER_01]: So yeah, and then, you know, cardless is probably my second most growing investment cardless, which now powers built.
• 31:25
  [SPEAKER_01]: which is very we love it and better work yeah you can screw over both you know Michael Spalph Bogos you'll cartless is a former intern of mine and I'm like God I feel old and funny enough his step-gram mother is my first boss at a college
• 31:46
  [SPEAKER_01]: So, the learning to keep your network never burning bridges, always keeping open with the people in your life, and I now know anyone that I know, even employees I didn't like, I never want to burn a bridge.
• 31:57
  [SPEAKER_01]: And I just tell the to everyone, because one single person, a person you sit next to on a flight can change your life.
• 32:02
  [SPEAKER_01]: So, yeah, I mean, I just now get incoming a ton of deals.
• 32:06
  [SPEAKER_01]: I also now
• 32:07
  [SPEAKER_01]: will speak at conferences like day or vc and I'm I talked to people.
• 32:12
  [SPEAKER_01]: I have a lot of friends Kevin Collarin.
• 32:14
  [SPEAKER_01]: I forget what venture of slow.
• 32:16
  [SPEAKER_00]: Yeah.
• 32:17
  [SPEAKER_01]: I mean, I forget which of our investments I met him through.
• 32:20
  [SPEAKER_01]: Now we call best together.
• 32:21
  [SPEAKER_01]: We share deals.
• 32:22
  [SPEAKER_00]: So slow is like so up your alley too.
• 32:23
  [SPEAKER_01]: I'm obsessed.
• 32:24
  [SPEAKER_01]: I'm Kevin Collarin is just
• 32:26
  [SPEAKER_00]: So we had Jack Reigns on the pod, do you know Jack?
• 32:28
  [SPEAKER_01]: Yeah.
• 32:28
  [SPEAKER_00]: The best.
• 32:29
  [SPEAKER_00]: Yeah.
• 32:29
  [SPEAKER_00]: He also wrote a book.
• 32:30
  [SPEAKER_00]: Yeah.
• 32:30
  [SPEAKER_01]: They're etiquette.
• 32:31
  [SPEAKER_01]: They did, I went to their etiquette.
• 32:32
  [SPEAKER_01]: You went to the etiquette, which was, yeah, spoke at it, which was a hoot.
• 32:36
  [SPEAKER_01]: So I'm just tickled by the VC world, having not come from.
• 32:40
  [SPEAKER_01]: I was a Spanish major in college.
• 32:42
  [SPEAKER_01]: I had a 2.8th University of Pittsburgh because I was so bored and class, but I was student body president, and like I said, I've always known, I'm going to be rich.
• 32:50
  [SPEAKER_01]: That was my biggest thing growing up.
• 32:52
  [SPEAKER_01]: I had mood boards, I would call them Mercedes, and get their glossy catalogs of all their cars.
• 32:57
  [SPEAKER_01]: I had it on my wall.
• 32:58
  [SPEAKER_01]: I just always knew I'd be successful, but I didn't academically, I knew that wasn't.
• 33:02
  [SPEAKER_01]: But my charisma, what I learned in
• 33:05
  [SPEAKER_01]: learning doing the student body president and in fraternity, I realize like I can engage with people and that's going to be how I get in and slowly but surely.
• 33:14
  [SPEAKER_01]: figured it out.
• 33:15
  [SPEAKER_00]: Yeah, well, that's what we learn in business, right?
• 33:16
  [SPEAKER_00]: It's like EQ is just most of the equation.
• 33:19
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• 33:26
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• 33:31
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• 33:32
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• 34:21
  [SPEAKER_00]: OK, so a quick experiment.
• 34:23
  [SPEAKER_00]: Think about the last long message you tight.
• 34:25
  [SPEAKER_00]: Could be a slack thread, a prompt in decline, maybe it's a detailed email.
• 34:28
  [SPEAKER_00]: It probably took you 10 minutes, maybe even 20, to get it right.
• 34:32
  [SPEAKER_00]: Now imagine you've just set it out loud instead.
• 34:34
  [SPEAKER_00]: That is the whole pitch for whisper flow.
• 34:36
  [SPEAKER_00]: whisper flow is voiced a text that actually works in every app on every device.
• 34:40
  [SPEAKER_00]: You speak naturally, and outputs clean, formatted text that's ready to send.
• 34:44
  [SPEAKER_00]: No set-up, no integrations, no fixing, weird transcription errors.
• 34:47
  [SPEAKER_00]: and it works across Gmail, Slack, No-Shane, Cloud, I-Message, wherever you type.
• 34:52
  [SPEAKER_00]: And unlike the built-in dictation on your phone, whisper flow removes all filler words, mid-sentence corrections, and jargon.
• 34:58
  [SPEAKER_00]: What I personally love about it too is that it perfectly matches my style.
• 35:01
  [SPEAKER_00]: So I often type in all lowercase letters, so it'll type like that.
• 35:05
  [SPEAKER_00]: I also say things like LMK, which means let me know in short-hand, and it'll auto adjust it from let me know to LMK.
• 35:11
  [SPEAKER_00]: Like many of you, I also do a lot of brain dumping into LLMs.
• 35:14
  [SPEAKER_00]: So instead of typing it all out, I actually just speak my windy train of thought into whisper flow, which is infinitely faster than trying to get my fingers to keep up with the pace of my thoughts.
• 35:23
  [SPEAKER_00]: If you do any serious writing or just send a lot of messages and emails, using whisper flow is a no-brainer.
• 35:28
  [SPEAKER_00]: Get one whole month of whisper flow pro completely free at ref.wisperflow.ai-sash trailblazers.
• 35:34
  [SPEAKER_00]: I want to talk about investing in things that are not connected to your brand, and how you think about that, because I mean, built in card lists, pretty obvious, connection there.
• 35:42
  [SPEAKER_00]: I would say morning, brew very obvious connection with newsletter.
• 35:45
  [SPEAKER_00]: If you want to feel old for a quick aside, one of our podcast sponsors, one of my investments is BeHeave.
• 35:52
  [SPEAKER_00]: which is an early morning brew employee.
• 35:54
  [SPEAKER_01]: Oh, interesting.
• 35:54
  [SPEAKER_00]: So we can throw it all the way back for you.
• 35:57
  [SPEAKER_00]: Everything's connected.
• 35:59
  [SPEAKER_00]: But I want to ask you about investing in things outside of things you know well.
• 36:02
  [SPEAKER_00]: Do you say, I don't do that at all.
• 36:04
  [SPEAKER_00]: I only want to get involved when I can be helpful.
• 36:06
  [SPEAKER_00]: And I have people to push it to.
• 36:09
  [SPEAKER_00]: Or do you like maybe do some healthcare?
• 36:11
  [SPEAKER_00]: Maybe do some climate, maybe do some vertical tasks?
• 36:13
  [SPEAKER_00]: How do you think about that investing outside of the areas you know well?
• 36:16
  [SPEAKER_01]: In general, I try to stick to what I know.
• 36:19
  [SPEAKER_01]: I did a liquor brand.
• 36:20
  [SPEAKER_01]: I've actually done two liquor brands.
• 36:22
  [SPEAKER_01]: The first one failed miserably double cross vodka.
• 36:24
  [SPEAKER_01]: That was actually my first investment years ago.
• 36:26
  [SPEAKER_01]: It was a friend of a friend.
• 36:27
  [SPEAKER_01]: the founder ended up dying, I think, in a DUI crash, it was horrible, and I lost, I don't know, 100K.
• 36:32
  [SPEAKER_01]: And that was when I didn't have a lot of money.
• 36:34
  [SPEAKER_01]: And I knew D'Danish didn't be doing this.
• 36:36
  [SPEAKER_00]: But it's also so ironic that you have a vodka brand and you die from, I mean, that's very bad.
• 36:40
  [SPEAKER_01]: So doing all the consumer goods, now, I have friends and VCs that are like, this company's growing, I recently invested in sales because I love the product.
• 36:48
  [SPEAKER_00]: Do you bull a pitch, guys?
• 36:49
  [SPEAKER_01]: Yes, I know Felix, so Felix Levine is a good friend.
• 36:51
  [SPEAKER_01]: So Felix will email me, like, look, this is gangbusters growing, so I'm like,
• 36:58
  [SPEAKER_01]: I believe, yeah, it's good to diversify some, but in general, I want to be behind brands.
• 37:03
  [SPEAKER_01]: I'm known for educating consumers on products that are going to make your life better.
• 37:08
  [SPEAKER_01]: So if the product makes people's lives better, makes a confusing topic, like points are confusing to people, I can help explain.
• 37:17
  [SPEAKER_01]: so that you can live your better, save money, travel better.
• 37:20
  [SPEAKER_01]: So that's like sort of the consensus.
• 37:24
  [SPEAKER_01]: I did recently invest in a sleep tech bed company through Felix and like, but those are not my core investments.
• 37:33
  [SPEAKER_01]: I like to do things where my network is immediately valuable, but I'm very particular with putting my full weight behind something and tell the products right.
• 37:43
  [SPEAKER_01]: So, yeah, I'm trying to actually slow down.
• 37:46
  [SPEAKER_01]: Now, I was saying you asked to a lot of different things and I want to be focused and mindful.
• 37:52
  [SPEAKER_00]: Totally.
• 37:53
  [SPEAKER_00]: Easier said than done, though, because when you're first getting started, everything sounds like a good idea.
• 37:56
  [SPEAKER_00]: You know?
• 37:57
  [SPEAKER_01]: I've had my certainly my fair share of bus.
• 37:59
  [SPEAKER_01]: And most of the bus that I've had, I've known deep down.
• 38:02
  [SPEAKER_01]: And some of them were in travel.
• 38:04
  [SPEAKER_01]: But, you know, my billionaire mentor friend was so bullish on it so I almost did it as a favor and then of course it didn't work out and so so those but as we all know you have to have the failures in order to gain the clarity you know listen to yourself again when you when you hear that voice being like this I don't think this is great like stop letting people hype you up.
• 38:24
  [SPEAKER_01]: But admittedly, I don't have, I do this myself.
• 38:26
  [SPEAKER_01]: I mean, I have lawyers and I don't do tons of diligence to be honest.
• 38:31
  [SPEAKER_01]: Yeah.
• 38:31
  [SPEAKER_01]: If I like the founder, that's a big thing for me, especially if the founder's exited.
• 38:37
  [SPEAKER_01]: But I'm trying not to do consumer product, certainly as Marshall says, no celebrity beverage.
• 38:45
  [SPEAKER_00]: It's tough.
• 38:45
  [SPEAKER_00]: I mean, Alex Cooper just shut down on the wall.
• 38:47
  [SPEAKER_01]: Let's talk about calling, calling water, unwell.
• 38:52
  [SPEAKER_00]: Yeah.
• 38:53
  [SPEAKER_01]: But yeah, it's a tough business.
• 38:54
  [SPEAKER_00]: It's a really tough business.
• 38:55
  [SPEAKER_00]: Is there a strategy around the number of deals you do in a year?
• 38:58
  [SPEAKER_00]: How you source them or is it really?
• 38:59
  [SPEAKER_00]: It sounds like it's quite ad hoc.
• 39:01
  [SPEAKER_00]: It's kind of just like whatever you have and think is right.
• 39:03
  [SPEAKER_01]: Yeah, I think each year now, I think if I can do six deals, I usually write between 50 and 150 and that's sort of like what I've been doing, but if anything great comes along.
• 39:17
  [SPEAKER_01]: But I'm staying within
• 39:19
  [SPEAKER_01]: the realm of loyalty, like the next generation of loyalty, because there is a big ship happening, you know, loyalty is more valuable than ever, loyalty programs which driving airlines is staying in business.
• 39:30
  [SPEAKER_01]: Airlines that have not invested in loyalty are folding by and large, so credit cards are booming and more and more people at points but still don't know how to use them.
• 39:41
  [SPEAKER_01]: I'm very interested in.
• 39:43
  [SPEAKER_01]: There's smart media technologies as a company that's a blockchain loyalty platform.
• 39:47
  [SPEAKER_01]: I believe that there's so much people so many miles and points sitting out there that go unused, which the banks don't love, by the way, because they need to count for them on their books.
• 39:56
  [SPEAKER_01]: So finding ways to tokenize loyalty.
• 39:59
  [SPEAKER_01]: So you've got 30,000 Southwest miles that you're never going to use.
• 40:05
  [SPEAKER_01]: You don't want to redeem them for gift card, but if you could tap to pay with those and get $200 spot treatment, like I know a lot of people would do that.
• 40:13
  [SPEAKER_01]: Airline would love that, because it's less than what it would be, so I'm trying to figure out, that's really what I love.
• 40:19
  [SPEAKER_00]: That's what you know well.
• 40:21
  [SPEAKER_00]: It makes perfect sense.
• 40:22
  [SPEAKER_00]: Yeah.
• 40:22
  [SPEAKER_00]: I want to ask you a question about the founders you like.
• 40:24
  [SPEAKER_01]: Yes.
• 40:25
  [SPEAKER_00]: And, you know, I'm preaching to the choir here, but from what I can tell from you and from your taste, Alex and Austin were very public facing founders.
• 40:34
  [SPEAKER_00]: honor extremely public facing founder you a tpg extremely public facing founder what's your take on how important it is for the founder to be public facing and I say that because you know both worlds very well you know creator media and you know business and making money what is your do you have a take on that on like I don't have to be you know what I think built has done very well is built has tons of influencers they work
• 41:00
  [SPEAKER_01]: with.
• 41:01
  [SPEAKER_01]: They have partners, you know, people true evangelists that spread the word, not, you know, encore being public and spreading the message is important.
• 41:11
  [SPEAKER_01]: But I actually like founders that realize the need for to get creators on board.
• 41:17
  [SPEAKER_01]: And that's like bullet pitch and what Felix and brother doing.
• 41:20
  [SPEAKER_01]: I love that, you know, the creator economy,
• 41:23
  [SPEAKER_01]: is not going away.
• 41:24
  [SPEAKER_01]: It's getting more influential, and the brands that realize their story telling can come from many different ways.
• 41:29
  [SPEAKER_01]: Like that's what I think is more impressive.
• 41:32
  [SPEAKER_01]: So the founders that I like are charismatic, and I want to see them building relationships with multiple, you know, what Uncle did with built is he didn't just build relationships with the banks.
• 41:42
  [SPEAKER_01]: He got all of the real estate partners onboard, and he's now diving deep in hospitality
• 41:50
  [SPEAKER_01]: he's just ultimately connected.
• 41:52
  [SPEAKER_01]: So I love founders who are connected, who aren't just coming to me being like, introduce me to every single person and making me do all the heavy lifting, on-core new tons of people.
• 42:02
  [SPEAKER_01]: So, yeah, a connected founder who realizes the importance of getting other people to tell the story is,
• 42:11
  [SPEAKER_01]: is my favorite kind.
• 42:12
  [SPEAKER_01]: Also founders who are communicative, I hate when people ghost me or you're too busy.
• 42:18
  [SPEAKER_01]: Why I'm busy too?
• 42:19
  [SPEAKER_01]: And I have 30 companies that I'm investing.
• 42:21
  [SPEAKER_01]: Just a simple update goes a long way.
• 42:23
  [SPEAKER_01]: So I dislike when founders go MIA.
• 42:27
  [SPEAKER_01]: And you know, you leave your investors thinking the worst.
• 42:31
  [SPEAKER_00]: 100% it's funny you make the comment about the most connected ones often don't need the help and I think that's a misconception and venture like you're supposed to be so helpful and sure you love helping these companies in the cardless built integration's great but in reality a lot of the best founders don't need you and so it's also balancing that like you want to be helpful but they also often don't need you when they're doing their own thing and I will say though when you need me when I have good ideas I want the founders to actually listen don't ignore me
• 42:59
  [SPEAKER_01]: But also it's I'm not the CEO.
• 43:02
  [SPEAKER_01]: I'm not the founder.
• 43:03
  [SPEAKER_01]: I'm going to give you my advice if you choose not to take it.
• 43:05
  [SPEAKER_01]: So be it But don't come complaining to me later when I was right, which I hate to tell you when it comes to like consumers cards loyalty What's going to happen in the landscape?
• 43:15
  [SPEAKER_01]: I'm ultimately plugged in in that space.
• 43:17
  [SPEAKER_01]: I read like I'm on my own Instagram all day I'm on Twitter every day like I'm constantly digesting and I have lots of good inputs for data So no one knows more than you
• 43:28
  [SPEAKER_01]: I mean, I mean, don't, don't get it.
• 43:31
  [SPEAKER_00]: I want to ask you a couple quick points questions.
• 43:33
  [SPEAKER_00]: OK, now that I have you here.
• 43:34
  [SPEAKER_00]: So you spend 16 years teaching people how to hack the system.
• 43:38
  [SPEAKER_00]: What is the single greatest hack that you cannot believe still works?
• 43:42
  [SPEAKER_01]: Well, I think what people don't use is technology.
• 43:45
  [SPEAKER_01]: So when I started the point, you just had to be an expert.
• 43:47
  [SPEAKER_01]: Airline website sucked, they didn't work.
• 43:50
  [SPEAKER_01]: Today, there are tools like Point Me, Seats.Aro, and I am an investor in Point Me.
• 43:56
  [SPEAKER_00]: But Seats.Aro is amazing.
• 43:59
  [SPEAKER_01]: You know, what seats that arrow will do, so if you want to fly, let's say Newark to Athens on Emirates business class, which there's tons of availability.
• 44:07
  [SPEAKER_01]: Today you have to kind of scroll on Emirates website one by one.
• 44:10
  [SPEAKER_01]: Seats that arrow can show you an entire year of routes, so whether that's Newark to Athens in business class and you can click a button and see an entire year of availability and then you plan your trip around.
• 44:21
  [SPEAKER_01]: availability, you can set alerts.
• 44:23
  [SPEAKER_01]: You can, you know, there's a tool for finding Latanza and on the pawn in JAL first class and, you know, really setting alerts for awards because airlines open up an inventory nonstop.
• 44:34
  [SPEAKER_01]: Another hack that people don't realize is last minute.
• 44:37
  [SPEAKER_01]: I'm pretty last minute.
• 44:38
  [SPEAKER_01]: I constantly change my plans which is great because airlines open up crazy amounts of award inventory at the lowest savered levels last minute.
• 44:46
  [SPEAKER_01]: I'm talking even one to seven days before the flight.
• 44:49
  [SPEAKER_01]: So say, you're always like, you know, people always say, well, I look in Delta's 500,000 miles every day.
• 44:55
  [SPEAKER_01]: Well, often they'll actually drop it to 200,000 miles a day before, but if you don't know to look, we're setting alert on seats that arrow, then you're paying the full price when you could just cancel and read a posit and rebook for cheaper amount on a different airline.
• 45:09
  [SPEAKER_01]: People don't realize most loyalty programs still let you cancel up until departure free of charge.
• 45:14
  [SPEAKER_01]: So when you're redeeming miles, that's a fully repundable ticket.
• 45:17
  [SPEAKER_01]: Keep looking for something better.
• 45:18
  [SPEAKER_01]: So say you want to, you know, so the lower awards open up non-stop,
• 45:23
  [SPEAKER_01]: There are sites out there called thrifty traveler's, a hundred bucks a year, and every day they send emails with drops of award inventory.
• 45:31
  [SPEAKER_01]: I've booked so many trips.
• 45:33
  [SPEAKER_01]: They'll send an email in no text you, too.
• 45:35
  [SPEAKER_01]: Amazing deal.
• 45:37
  [SPEAKER_01]: Fiji is on sale with Fiji Air, and because the airline sometimes they just release tons of inventory, whether it's their systems recalibrating, but it only lasts like a day.
• 45:47
  [SPEAKER_01]: So people, if you subscribe to thrifty traveler,
• 45:50
  [SPEAKER_01]: plan your trips around where the amazing inventory is.
• 45:53
  [SPEAKER_01]: There'll be Australia, Australia during New Year's was like 60,000 points, crazy.
• 45:59
  [SPEAKER_00]: And such a bucket list thing to do.
• 46:00
  [SPEAKER_01]: Right, so paying $100 to have 365 days of deals, like even if you just choose one deal, that can, so letting other people do the hard work for you is my biggest step.
• 46:10
  [SPEAKER_00]: I love it, leverage technology.
• 46:11
  [SPEAKER_00]: You're saying that you're an investor in this context.
• 46:13
  [SPEAKER_00]: I'm like, I agree with you.
• 46:15
  [SPEAKER_00]: What's the single greatest savings you've ever had on a booking?
• 46:19
  [SPEAKER_01]: Well, I'm a first class horror.
• 46:23
  [SPEAKER_01]: There I said it.
• 46:25
  [SPEAKER_01]: I want to make a warning to everyone.
• 46:28
  [SPEAKER_01]: If you're comfortable in the class of service, you're currently flying, whether that's economy, premium economy, do not change that.
• 46:34
  [SPEAKER_01]: Because once you start dabbling in the dark arts of business and international first class is so hard to go back and it will be an expensive life long.
• 46:45
  [SPEAKER_01]: habit.
• 46:46
  [SPEAKER_01]: So I am all about first class and international first class is insanely expensive.
• 46:52
  [SPEAKER_01]: Here's a tip that I still live tons of, for example, it doesn't let you redeem most miles for their first class.
• 46:59
  [SPEAKER_01]: But they do let you upgrade.
• 47:01
  [SPEAKER_01]: So I'm flying to Johannesburg from Frankfurt, and it was $10,000 for first class.
• 47:08
  [SPEAKER_01]: And even though I can expense it fundamentally, like just, it is against my DNA to pay full price.
• 47:13
  [SPEAKER_01]: It would be a Charlotton.
• 47:15
  [SPEAKER_01]: But what I did was I booked a $3,000 business class flight.
• 47:19
  [SPEAKER_01]: and instantly Lyfton selects you, see if there's an upgrade to first class.
• 47:22
  [SPEAKER_01]: So here's what you do.
• 47:23
  [SPEAKER_01]: You book a flight because all the airlines allow you to cancel within 24 hours with Lyfton.
• 47:28
  [SPEAKER_01]: So you book business, ticket it, and then see instantly for me today.
• 47:32
  [SPEAKER_01]: I did this right on the street before this podcast.
• 47:34
  [SPEAKER_01]: It was like fingers crossed $1,800.
• 47:36
  [SPEAKER_01]: So $3,000 ticket and $1,800 to get first class in the 747 and on an 11 hour flight versus paying $10,000.
• 47:43
  [SPEAKER_01]: Twice as much if I just would have booked it out right.
• 47:46
  [SPEAKER_01]: So,
• 47:46
  [SPEAKER_00]: unbelievable.
• 47:47
  [SPEAKER_00]: That's pretty good savings and haven't just right outside.
• 47:49
  [SPEAKER_01]: Right outside.
• 47:50
  [SPEAKER_01]: 50% off.
• 47:50
  [SPEAKER_00]: More than 50%.
• 47:51
  [SPEAKER_00]: Truly.
• 47:52
  [SPEAKER_00]: Wow.
• 47:52
  [SPEAKER_00]: Unbelievable.
• 47:52
  [SPEAKER_00]: I will say when you walked in the door and I'm sure you get this all the time.
• 47:56
  [SPEAKER_00]: You're so tall.
• 47:57
  [SPEAKER_00]: Pretty tall.
• 47:58
  [SPEAKER_00]: Like, but in a wonderful way, okay?
• 48:00
  [SPEAKER_01]: Broad.
• 48:00
  [SPEAKER_01]: My shoulders are so wide that I don't fit in most business class.
• 48:03
  [SPEAKER_00]: Yeah, like it's like, I wonder if, you know, I, I'm so small, do I, do I, do I dabble or do I just never do I just never stick and, you know, say in a call to me forever.
• 48:12
  [SPEAKER_01]: Well, how many points do you have?
• 48:13
  [SPEAKER_00]: Like, you know, I so many, I so many, but the problem my problem and this is the other thing I'd love to get your take on is I just use like Mx platinum and Chase.
• 48:21
  [SPEAKER_01]: Yeah.
• 48:21
  [SPEAKER_00]: And I just rack up points.
• 48:23
  [SPEAKER_00]: Yep.
• 48:23
  [SPEAKER_00]: And I don't even look at it from like busy and.
• 48:26
  [SPEAKER_00]: You know, for people like that, they're not optimizing, they're not opening the new problems.
• 48:29
  [SPEAKER_01]: That's the point me.
• 48:30
  [SPEAKER_01]: And by the way, if you have MX.me slash MX is free for MX card holders, and it'll tell you.
• 48:35
  [SPEAKER_01]: So you want to New York to Paris.
• 48:36
  [SPEAKER_01]: It'll say, oh, transfer to
• 48:38
  [SPEAKER_01]: Air Canada, it's a book on United for 60,000 or Air France has it for 90,000 and it'll just do it all for you and it shows live availability so you can just transfer and book it.
• 48:48
  [SPEAKER_00]: Okay, I'm going to try point me.
• 48:49
  [SPEAKER_00]: I haven't done that one yet.
• 48:50
  [SPEAKER_01]: Point me is excellent.
• 48:51
  [SPEAKER_01]: I also, if you have MX Platinum, I would get an MX Gold card in tandem because the Gold card is 4x on dining and groceries which you spend a lot on.
• 48:59
  [SPEAKER_01]: MX is only 1x on everything and then 5x on Airfare and some other travel.
• 49:09
  [SPEAKER_01]: favorite amongst points experts.
• 49:11
  [SPEAKER_00]: Okay, I've never even heard of the gold card.
• 49:13
  [SPEAKER_00]: Wow, you're legit.
• 49:13
  [SPEAKER_00]: Okay.
• 49:13
  [SPEAKER_00]: Okay.
• 49:14
  [SPEAKER_01]: Okay.
• 49:14
  [SPEAKER_00]: Let's have a new every day.
• 49:15
  [SPEAKER_00]: Last question, we'll get to our trade-offs.
• 49:17
  [SPEAKER_00]: You have beautiful children.
• 49:20
  [SPEAKER_00]: Do they fly with you?
• 49:21
  [SPEAKER_00]: International first-class?
• 49:22
  [SPEAKER_00]: They do.
• 49:22
  [SPEAKER_01]: And they're nanny as well.
• 49:24
  [SPEAKER_01]: I'm like a big believer in We all fly together.
• 49:27
  [SPEAKER_01]: Sometimes I'll be in first with one kid and like
• 49:29
  [SPEAKER_01]: because you can't get availability, and I'm not spending crazy amounts for them to find first, but like the nanny will always be in at least business or first.
• 49:38
  [SPEAKER_01]: And for the most part, the well-behaved, there was a Korean air flight, somewhat recently where my toddler just, the problem with kids is when they get over tired, they become demonic, and he didn't want to sleep and started screaming, and I did feel kind of guilty that we're in.
• 49:53
  [SPEAKER_01]: first class and people are paying a lot of money.
• 49:55
  [SPEAKER_01]: It did my best, he did eventually go down.
• 49:57
  [SPEAKER_01]: But I like to say to people, if you want to control the manifest on the plane you're flying on, you are more than welcome to charter.
• 50:04
  [SPEAKER_01]: Otherwise, he didn't bring it to you, but planes, even business class, are public transportation.
• 50:08
  [SPEAKER_00]: And it's a good reminder for the people that always fly first and never have to experience a crying baby.
• 50:12
  [SPEAKER_00]: This is what real life is like.
• 50:13
  [SPEAKER_01]: Yeah.
• 50:13
  [SPEAKER_01]: Now, generally, we'll just get a pair of headphones that are really good, Bose, QC, Ultra's, are amazing, even if sometimes it's a crime maybe it can still get through them, but here's my tip, put ear plugs in your ears and then put noise canceling over it.
• 50:29
  [SPEAKER_00]: Wow, double whammy.
• 50:30
  [SPEAKER_01]: Double whammy.
• 50:31
  [SPEAKER_00]: Okay, I love it.
• 50:32
  [SPEAKER_00]: We're full of tips today.
• 50:33
  [SPEAKER_00]: Yes.
• 50:33
  [SPEAKER_00]: So here's a problem I hear constantly from operators.
• 50:36
  [SPEAKER_00]: The data exists.
• 50:37
  [SPEAKER_00]: The answers are somewhere in there, but getting to that actually pulling a useful insight without bugging the data team or learning SQL takes way too long or just does not happen.
• 50:46
  [SPEAKER_00]: Hex solves that.
• 50:47
  [SPEAKER_00]: Hex is an AI analytics platform where anyone on your team can ask data questions and plain English and get real answers backed by your actual business context.
• 50:56
  [SPEAKER_00]: No SQL required.
• 50:57
  [SPEAKER_00]: And the best part is that hex shows you exactly how it's data agents think, so you can see where the logic comes from and trust the output.
• 51:04
  [SPEAKER_00]: The more your team uses it, the smarter it gets.
• 51:06
  [SPEAKER_00]: From seed stage founders running lean to larger orgs dealing with serious data complexity, hex is built to scale with you.
• 51:12
  [SPEAKER_00]: It's game-changing for people like me who want to understand what's going on under the hood, but we are not the data experts.
• 51:17
  [SPEAKER_00]: It's funny too, because I feel like every time I look over my operator friend's shoulders, whether they're in product, or marketing, or ops, they often have a hex dashboard pulled up.
• 51:25
  [SPEAKER_00]: It's a great tool.
• 51:26
  [SPEAKER_00]: Trailblazers listeners get an exclusive 30-day free trial at hex.ai slash trailblazers.
• 51:31
  [SPEAKER_00]: Um, let's get to our trailblazers rate offs, okay?
• 51:34
  [SPEAKER_00]: Let me know what comes to mind first.
• 51:35
  [SPEAKER_00]: Book in hand or podcast in ears.
• 51:37
  [SPEAKER_01]: Book in hand.
• 51:38
  [SPEAKER_00]: Any favorites recently?
• 51:40
  [SPEAKER_01]: So I do a lot of work with Nobel Peace Prize winners.
• 51:42
  [SPEAKER_01]: And one of my favorite books is Lame of Bowie.
• 51:45
  [SPEAKER_01]: Might be our powers.
• 51:47
  [SPEAKER_01]: It is about her journey from being a refugee to a Nobel Peace Prize winner.
• 51:50
  [SPEAKER_01]: And it's just those stories.
• 51:52
  [SPEAKER_01]: Like, you know, if you're getting hitting robots in business, when you read the stories of Nobel Peace Prize winners who have, like, defied odds to end civil wars, I believe everything's about perspective.
• 52:02
  [SPEAKER_00]: I love that, makes you grateful instantly.
• 52:04
  [SPEAKER_01]: Instantly.
• 52:04
  [SPEAKER_00]: It's a dose of reality.
• 52:05
  [SPEAKER_01]: Check you back.
• 52:06
  [SPEAKER_01]: Yeah, bring you back to Earth.
• 52:07
  [SPEAKER_00]: I love that.
• 52:08
  [SPEAKER_00]: Higher slow or fire fast.
• 52:13
  [SPEAKER_01]: I think higher slow is a smarter decision.
• 52:18
  [SPEAKER_01]: That's what I did.
• 52:19
  [SPEAKER_01]: I mean, it's somewhere in between, but I don't believe in firing fast.
• 52:24
  [SPEAKER_00]: Okay.
• 52:25
  [SPEAKER_00]: Ten small wins are one big moon shot one big moon shot.
• 52:29
  [SPEAKER_01]: Oh, tell me more.
• 52:30
  [SPEAKER_01]: Yeah, just go bigger.
• 52:31
  [SPEAKER_01]: Go home.
• 52:31
  [SPEAKER_01]: This is story of my life.
• 52:32
  [SPEAKER_01]: Like go for it.
• 52:34
  [SPEAKER_00]: Love it.
• 52:34
  [SPEAKER_01]: Because I feel like small little wins get people distracted from a big vision and companies that are just doing small things all the time.
• 52:40
  [SPEAKER_01]: I don't think really ever achieve greatness.
• 52:43
  [SPEAKER_00]: We're listening to Celine Dion.
• 52:44
  [SPEAKER_00]: So you just listen to one song.
• 52:46
  [SPEAKER_00]: It's a new moon shot.
• 52:47
  [SPEAKER_01]: Have an out-of-body experience and just start making your rational decisions.
• 52:51
  [SPEAKER_00]: I love it.
• 52:52
  [SPEAKER_00]: I love it.
• 52:52
  [SPEAKER_00]: It's almost scary.
• 52:53
  [SPEAKER_00]: Your whole life will go in flux if you listen to too much to lean.
• 52:56
  [SPEAKER_00]: Being early or being right.
• 52:57
  [SPEAKER_01]: I think being early.
• 53:02
  [SPEAKER_01]: Actually no, in entrepreneurship.
• 53:06
  [SPEAKER_01]: Early is not always better.
• 53:07
  [SPEAKER_01]: I think coming correct later with the better strategy.
• 53:10
  [SPEAKER_01]: I think so many startups that come later, better, end up winning.
• 53:14
  [SPEAKER_00]: Okay.
• 53:16
  [SPEAKER_00]: What's the best teacher and mentor or a mistake?
• 53:19
  [SPEAKER_01]: Mistake.
• 53:20
  [SPEAKER_00]: Okay, I need that come to mind that you're like, learned a lot.
• 53:28
  [SPEAKER_01]: Is me realizing I was not a great people manager for years.
• 53:32
  [SPEAKER_01]: I kind of knew that, but it wasn't until I really had a business coach come in and was like, she interviewed all my employees and I had this oh shit moment.
• 53:40
  [SPEAKER_01]: Like, I'm not a good manager, but no one would have been able to tell me that unless I had made those mistakes.
• 53:46
  [SPEAKER_01]: You know, so,
• 53:49
  [SPEAKER_01]: I'm not a big believer in like self-help, like trying to foresee life's problems, like you just have to go with it and hopefully beware enough when you make mistakes, wait a minute.
• 53:58
  [SPEAKER_01]: I'm not supposed to be doing that.
• 54:00
  [SPEAKER_00]: Yeah, but you, you seem like someone who is just so self-aware that like if someone confronts you like, hey, I think you're not going to do this thing, people managing, you'll hear it.
• 54:07
  [SPEAKER_01]: I did, but unfortunately for so many years, I didn't have that person that even tell me.
• 54:11
  [SPEAKER_00]: Yeah, what made you want to get a coach in the first place?
• 54:14
  [SPEAKER_01]: I think at that time, I was actively melting down burning out.
• 54:19
  [SPEAKER_01]: And the company, Red Ventures, was like, hey, you can have the executive coach that is our CEO's longtime advisor, and she's going to come up and help you and sit down and like, great, let's do it.
• 54:30
  [SPEAKER_01]: And then she's like, I'm going to interview all your employees.
• 54:34
  [SPEAKER_01]: And we sat down and she's like, let's have it.
• 54:35
  [SPEAKER_01]: And I remember exactly time and place.
• 54:37
  [SPEAKER_01]: And it was like, you know, what's it?
• 54:40
  [SPEAKER_01]: The Emperor has no clothes, and I'm like,
• 54:43
  [SPEAKER_01]: And then yeah, it was like yeah, when you're reality because on business business blowing up We're popular everything's great, and then when the reality hit of like weight of it I am not being a great boss, and this is not who I was raised my parent, you know So and I give myself grace because it was tons of pressure to deliver grow and I'm managing my brand with a new parent company trying to that's a lot
• 55:09
  [SPEAKER_00]: And most people will run away, and so I think it says so much, you know, it's not about like when you how many times you fall, but it's how you get back up or whatever that line is, you were like, okay, I hear it, now how can I slot in versus being like, I am a good people manager or screw you all in leaving you know, I respect the grace you had through it.
• 55:26
  [SPEAKER_01]: Yeah, well, I respect the grace that red ventures had for me.
• 55:28
  [SPEAKER_01]: They knew it and instead of just,
• 55:31
  [SPEAKER_01]: you know, hey, we're taking this away today and making me feel like, hey, I might just want to get out of here, which maybe I would have done because I also was just burnout that we came to it together through analysis and feedback and unfilled.
• 55:46
  [SPEAKER_01]: And I just think to founders out there, I implore you to figure out a way to get
• 55:52
  [SPEAKER_01]: Uncellus, you know, true feedback.
• 55:54
  [SPEAKER_01]: Not one on one's where your directs are telling you everything's great, because there always will be that power to buy, and your directs have to pay for school.
• 56:01
  [SPEAKER_01]: And families and they're not going to ever really tell you the truth.
• 56:05
  [SPEAKER_01]: Like getting a business coach that you can have, get in the weeds, and then deliver it and be open to receiving it is the biggest, you know, management gift that I've ever been given.
• 56:15
  [SPEAKER_00]: Yeah.
• 56:15
  [SPEAKER_01]: It's not to say, no, I won't return to management one day, but I will return to it with a complete different mindset.
• 56:21
  [SPEAKER_00]: And with someone right by your side to help make sure you're doing it in the way that feels aligned but also serving others.
• 56:26
  [SPEAKER_00]: Yeah, I hear you.
• 56:28
  [SPEAKER_00]: Is the future of AI abundance or chaos?
• 56:31
  [SPEAKER_01]: I'm a eternal optimist.
• 56:33
  [SPEAKER_01]: I think it's abundance.
• 56:34
  [SPEAKER_00]: Okay, love that.
• 56:36
  [SPEAKER_00]: Killer product or loyal niche audience.
• 56:38
  [SPEAKER_01]: Loyal niche audience.
• 56:39
  [SPEAKER_00]: Okay, tell me more.
• 56:40
  [SPEAKER_01]: I think if you develop the audience that cares deeply for you, you can
• 56:46
  [SPEAKER_01]: Continuously evolve and I think you got to start with the loyal audience and giving them a lot like we did with built The built product has changed built has made mistakes with product, but built is still growing even through mistakes because the audience, which has been given so much value through their point system through their promotions That company still doing well, so I think
• 57:11
  [SPEAKER_01]: so many companies sit and wait and try to evolve and have a perfect product versus just getting in the weeds, listening to their consumers, understanding the pain points in the consumer process and then building.
• 57:22
  [SPEAKER_01]: Once you have people's trust, you can continue to evolve and completely change the product because, you know, throughout time, the product's going to need to change anyways, so start with the audience, build the loyal, build trust and listen.
• 57:34
  [SPEAKER_00]: Absolutely.
• 57:35
  [SPEAKER_00]: when you're the expert at that.
• 57:36
  [SPEAKER_00]: That's why I was excited to hear your answer because you know if you if you didn't say that, I would be like, oh, something's wrong.
• 57:40
  [SPEAKER_00]: Floor, yeah, exactly.
• 57:42
  [SPEAKER_00]: VC or bootstrapping.
• 57:44
  [SPEAKER_01]: I think bootstrapping, I booked, I know I spent $10.
• 57:47
  [SPEAKER_01]: I know my case is very unique, but.
• 57:52
  [SPEAKER_01]: You know, if you can bootstrap, I think you can start a lot of companies, especially with AI now and being able to code and to map things out and do research and like you can do a lot as we're seeing with many, you know, billion dollar founders with one, two, three employees.
• 58:06
  [SPEAKER_01]: So, of course, VC money is important when you need to scale and hit, hit strike while the iron's hot, but I would, I think people think VC money is so easy.
• 58:17
  [SPEAKER_01]: Let's get it, but that is not the mindset I would do if I did it again.
• 58:20
  [SPEAKER_00]: You know, it's funny, you're a perfect case study in this because you sold your company for 28 million and you owned presumably all of it.
• 58:29
  [SPEAKER_00]: I can't tell you how many founders have their company for billions and walk away with less than 28 million.
• 58:33
  [SPEAKER_01]: Yeah, I get served those on my algorithm all the time.
• 58:36
  [SPEAKER_01]: The founders who break down the math, yeah.
• 58:38
  [SPEAKER_01]: it's insane and also yet you're not being able to pay yourself you know you're getting a founder salary and then not a great payout whereas if you would have just kept more equity and just paid yourself more.
• 58:51
  [SPEAKER_00]: Yeah, it's, it's wild.
• 58:53
  [SPEAKER_00]: It's wild.
• 58:54
  [SPEAKER_00]: Okay, never post on social media again, where we're going to like bundle writing into that.
• 58:58
  [SPEAKER_00]: Okay, never do like another blog post again.
• 59:00
  [SPEAKER_00]: And this is all connected to like you and the points guy or never raise another dollar ever again, will never raise another dollar never we're profitable.
• 59:09
  [SPEAKER_01]: Okay.
• 59:11
  [SPEAKER_01]: And yeah, we would.
• 59:14
  [SPEAKER_01]: TBG doesn't raise money.
• 59:15
  [SPEAKER_01]: We've never raised money.
• 59:16
  [SPEAKER_00]: What about for a future business?
• 59:18
  [SPEAKER_01]: Um, once again, I mean, if I can do it once, I can do it twice.
• 59:21
  [SPEAKER_01]: Let's create really cool content.
• 59:23
  [SPEAKER_01]: Let's like it.
• 59:24
  [SPEAKER_01]: Let's, you know, give the people what they need and travel.
• 59:26
  [SPEAKER_01]: I still think there's a lot that needs to be done.
• 59:29
  [SPEAKER_01]: So, you know, even even elsewhere, yeah, posting and content and owning an audience.
• 59:34
  [SPEAKER_01]: I feel like there's so many ways to monetize that.
• 59:36
  [SPEAKER_00]: I love that.
• 59:36
  [SPEAKER_00]: What is the number one thing that is missing in travel right now?
• 59:40
  [SPEAKER_01]: I think intelligent.
• 59:44
  [SPEAKER_01]: travel planning, you know, AI is helpful.
• 59:48
  [SPEAKER_01]: I so believe in AI for travel, you know, I say fancy hotels, and I, when I went to Australia last year, wanted to plan, you know, stuff for my kids, I wanted to charter a boat, and it would be one day between every email with the time change with the
• 1:00:05
  [SPEAKER_01]: wildly overrated in most cases, or some hotels, they do it great, but I think the Consiers model is distant, it's informal, it's the incentives are not aligned, and I think people think they're getting ripped off.
• 1:00:20
  [SPEAKER_01]: So I think AI really needs to, and it is, you know,
• 1:00:25
  [SPEAKER_01]: improving vastly and helping you plan a fully curated trip.
• 1:00:30
  [SPEAKER_01]: But I also believe in like travel at luxury travel advisors are booming.
• 1:00:33
  [SPEAKER_01]: So blending, you know, having a luxury travel advisor with the human touch with AI.
• 1:00:38
  [SPEAKER_01]: But yeah, it's still a full time job sometimes to plan.
• 1:00:41
  [SPEAKER_01]: I wanted to do two weeks in Europe.
• 1:00:44
  [SPEAKER_01]: Understanding what the on the ground situation is, understanding weather, which, you know, hot take, you summer is overrated as someone who does it every year.
• 1:00:52
  [SPEAKER_01]: I'm really rethinking that for next year.
• 1:00:54
  [SPEAKER_00]: So was it a bearable this year?
• 1:00:55
  [SPEAKER_01]: Unbearable.
• 1:00:56
  [SPEAKER_01]: I was supposed to go to Paris.
• 1:00:57
  [SPEAKER_01]: It was 99 degrees, which I was like, this is unsafe for children.
• 1:01:00
  [SPEAKER_01]: So we canceled Paris, went to Portugal.
• 1:01:03
  [SPEAKER_01]: Tuscany was 90 and just roasting.
• 1:01:06
  [SPEAKER_01]: Did you get a camera this year?
• 1:01:07
  [SPEAKER_01]: No.
• 1:01:08
  [SPEAKER_00]: because I've seen, you see, the can, pictures, and videos, they're just melting, everyone.
• 1:01:12
  [SPEAKER_01]: It's not enjoyable, so.
• 1:01:14
  [SPEAKER_00]: Yeah, I hear you.
• 1:01:16
  [SPEAKER_00]: Okay, last and final question.
• 1:01:17
  [SPEAKER_00]: It's hard to kind of what we're saying here, but is AI overhyped or underhyped?
• 1:01:20
  [SPEAKER_01]: I think it's underhyped.
• 1:01:22
  [SPEAKER_01]: I think it's changed my life dramatically, and I'm still not fully utilizing it.
• 1:01:27
  [SPEAKER_01]: I'll just say from my personal side,
• 1:01:30
  [SPEAKER_01]: having multiple investments, having traditional investments, and having a fancy, high net worth advisor, one of the biggest issues I've had in my life is calculating my net worth.
• 1:01:40
  [SPEAKER_01]: Like, carda, pulley, cake, and then all my investments, I do a lot of some crypto, private equity, I had my financial life,
• 1:01:54
  [SPEAKER_01]: You know, it's doing well over all, but it's impossible because my financial advisor doesn't want to touch this stuff.
• 1:02:00
  [SPEAKER_01]: Card is not integrating with fidelity.
• 1:02:01
  [SPEAKER_01]: You know, like, so I think, you know, there is a new tool called Arch, which I just started you.
• 1:02:07
  [SPEAKER_01]: I was just about to tell you about Arch.
• 1:02:08
  [SPEAKER_01]: Polls a lot.
• 1:02:09
  [SPEAKER_01]: And so that has been a, a God said.
• 1:02:11
  [SPEAKER_00]: I literally thought to be like, I have a wreck for you there.
• 1:02:13
  [SPEAKER_00]: Ryan's company.
• 1:02:14
  [SPEAKER_00]: He's amazing.
• 1:02:14
  [SPEAKER_01]: amazing.
• 1:02:15
  [SPEAKER_01]: Yeah.
• 1:02:15
  [SPEAKER_01]: So I love arts and I'd like sign on.
• 1:02:17
  [SPEAKER_01]: I was like, can I invest too?
• 1:02:18
  [SPEAKER_01]: You know, they're crushing it.
• 1:02:18
  [SPEAKER_00]: They're crushing it.
• 1:02:19
  [SPEAKER_00]: They're crushing it.
• 1:02:20
  [SPEAKER_00]: Everyone meet the founder.
• 1:02:20
  [SPEAKER_00]: I can see it.
• 1:02:21
  [SPEAKER_01]: But I think like real life problems like AI has been, you know, dramatically improving my life.
• 1:02:26
  [SPEAKER_01]: So I think we are just touching the surface of how AI can make our lives better.
• 1:02:32
  [SPEAKER_00]: Absolutely.
• 1:02:34
  [SPEAKER_00]: Brian, thank you for being here.
• 1:02:34
  [SPEAKER_00]: This was super fun.
• 1:02:36
  [SPEAKER_00]: I appreciate it.
• 1:02:36
  [SPEAKER_01]: Safe travel is in, you just start spurreding on business class.
• 1:02:39
  [SPEAKER_01]: Oh, I think you might have.
• 1:02:40
  [SPEAKER_01]: You only look like one.
• 1:02:41
  [SPEAKER_00]: Like once in a while, you know what I mean?
• 1:02:42
  [SPEAKER_00]: I got it.
• 1:02:43
  [SPEAKER_01]: Yeah.
• 1:02:43
  [SPEAKER_00]: Got it.
• 1:02:44
  [SPEAKER_00]: Thanks so much for listening to The Trailblazers podcast.
• 1:02:46
  [SPEAKER_00]: If you found this conversation valuable, please follow along on socials, share with a friend, leave a review, all the things.
• 1:02:53
  [SPEAKER_00]: Most of all, please subscribe to our channel.
• 1:02:55
  [SPEAKER_00]: It helps more contrain builders find us and supports the work we're doing here.
• 1:02:58
  [SPEAKER_00]: To learn more about what we're doing, you can visit trailblazerspod.com or my venture capital firm parkrangerscaped.com or just follow along on socials at Erica UnderscoreWinger.
• 1:03:08
  [SPEAKER_00]: Until next time, keep trailblazing.