#861: 4-Hour Workweek Success Story Brian Dean — From Dad’s Basement to Selling Two Companies

Summary

The Tim Ferriss Show – Episode #861

Guest: Brian Dean
Title: 4-Hour Workweek Success Story — From Dad’s Basement to Selling Two Companies
Date: April 16, 2026

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Overview

This episode serves as a 4-Hour Workweek case study, featuring Brian Dean, founder of Backlinko and Exploding Topics. Brian shares his journey from being broke in his dad’s basement to founding and exiting two successful companies, both ultimately acquired (Backlinko by Semrush, and Semrush itself by Adobe). Tim and Brian dive deep into actionable tactics: geoarbitrage, building and automating a muse business, learning SEO, surviving Google’s infamous search updates, selling companies, and (crucially) what to do with your life once you’ve achieved financial freedom.

The conversation is rich with practical lessons, candid missteps, and reflections on psychological challenges post-success, especially the rarely discussed issue of “filling the void.” The tone is straightforward but often humorous and self-deprecating, with detailed anecdotes and advice for aspiring entrepreneurs.

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Key Discussion Points & Insights

1. Origin Story: Hitting Rock Bottom & Discovering The 4-Hour Workweek

[03:16-05:21]

• Brian left an unfulfilling PhD program and struggled to find work during the 2008 financial crisis, moving into his dad’s basement.
• Initial business idea: create a search engine for nutrition questions; had no business experience.
• Discovers and commits to The 4-Hour Workweek, following it literally, step by step:

  “I was like, I’m not gonna go to the next page until I’m ready. Good and ready... I just followed the book exactly as it was written.” – Brian Dean [05:53]

2. First Business Experiments & Early Failures

[06:05-12:31]

• His first product, an ebook about nutrition for back pain, flopped—no traffic, no sales.

• Realizes the challenge is getting “free traffic”; stumbles upon SEO as a potential solution.

• Starts building hundreds of “exact match” micro-niche sites for AdSense revenue, scaling up to 200+ domains.

  “The idea is that you scale up enough and take a few steps later you got a private island or something.” – Brian Dean [09:26]

• Experiences the brutal impact of Google’s Panda update, which wipes out his “thin content” sites overnight.

  “It was like one day they push a button and, you know, thousands of websites got completely obliterated, including mine.” – Brian Dean [11:58]

• Learns the danger of building on shaky foundations and pivoting away from black-hat SEO.

3. Lifestyle Design & Geoarbitrage

[10:48-11:26, 47:31-48:45]

• Dreamlining and financial targets: Initially, the goal is simply to “get out of the basement,” but after experiencing life in Asia, $3K/month passive income becomes the main target.
• Discovers and embraces geoarbitrage—living “like a king” on a modest income in Thailand and later, Berlin.

  “If you can get 3K a month in Thailand, you can live like a king... that was my entire focus.” – Brian Dean [11:01]

4. Building a Real, Resilient Business

[12:31-14:45]

• Motivated by repeated Google penalties, shifts to building credible content sites (“white-hat SEO”) in personal finance.
• Frustrated by generic advice in the SEO world, he aspires to provide the clarity he couldn’t find elsewhere.

5. Founding Backlinko: The 10x Content Playbook

[18:02-23:02]

• Launches Backlinko to offer actionable, in-depth SEO advice—filling the content gap he’d noticed.

• Initially tries the "publish and pray" model (high output, low impact), before switching to a “quality over quantity” approach. Major breakthrough comes from investing 25+ hours into a single “200 ranking factors” epic blog post.

  “I just threw out the whole playbook... I’m just going to put out something once a month and it’s going to be the best thing on that topic that’s ever been written by 10x.” – Brian Dean [22:28]

6. The Backlinko Acquisition and Lessons on Selling

[23:02-29:24]

• Semrush’s acquisition: initially ignored outreach, mistaking it for spam; eventually leads to a deal after an intense, drawn-out due diligence process.

• Tim breaks down why clear documentation, especially with independent contractors, is essential for sellable businesses.

• Brian echoes this, warning that it turned out to be the biggest time sink during the sale.

  “Even people that ghosted me... I still had to reach out to those people. Of course they’re not going to reply, but you have to show that you tried.” – Brian Dean [28:19]

• Keep clean finances and agreements from the start; Brian did better the second time.

7. What Happens After You Sell: Filling the Void

[34:19-35:42, 50:20-54:30]

• Even a business running on autopilot (3 hours/week) can leave you bored or purposeless.

  “Honestly, I wasn’t filling the void... and then started another startup.” – Brian Dean [35:05]

• After selling both companies, experiences stress and listlessness despite “being set for life”; attributes it partly to loss of direction and structure.

• Hard reset: travel and time off (a trip to Portugal) helps rebalance.

• Replaces the urge for another startup with tennis, which provides exercise, social interaction, fun, community, and purpose.

  “Tennis... just one activity, fills almost all of these... Checks all the boxes and fills this void. It’s amazing, man.” – Brian Dean [53:01]

• Tim underscores the importance of “filling the void” as an essential, but overlooked, component of lifestyle design.

8. Founding and Growing Exploding Topics: New Lessons

[32:52-38:41]

• Motivation wasn’t purely financial; sought novelty and excitement after automating Backlinko.

• Initial monetization mistake: tried to run a paid newsletter rather than SaaS; quickly learned users wanted customizable, niche trend reports.

  “Sometimes you just need to get that beating over your head.” – Brian Dean [37:19]

• Major win: focusing on “data-driven” content—being the reliable source for specific stats, especially those sought after by journalists and bloggers (e.g., “how many users does ChatGPT have?”)

  “If you publish one of the first or the first specific stats page, then you get into this virtuous cycle where you’re very visible when someone’s searching for that topic.” – Brian Dean [38:51]

9. Advice & Frameworks for Entrepreneurs

[41:00-44:06]

• Best business advice: From Noah Kagan — “Double down on what works.”

  “It’s so rare that you find something that works... if you can find one thing that works and scale it up, that can get you pretty far.” – Brian Dean [41:32]

• Book Recommendations:

  • Ready, Fire, Aim by Michael Masterson — for action-oriented entrepreneurship.

  “This gets you going on the most important things... The key is really starting, starting, starting.” – Brian Dean [43:01]

  • Built to Sell by John Warrilow for those considering company exits.

• Start lean: Backlinko cost a few hundred dollars to launch; Exploding Topics required ~$90K due to acquisition of an existing prototype and technical partner.

10. Miscellaneous Lessons and Anecdotes

• Adjusting to new cost-of-living realities and verifying geoarbitrage opportunities—price references in books can become outdated.
• Funny story: Arriving in Berlin expecting palatial apartments based on old Craigslist ads from The 4-Hour Workweek, only to find they’re mostly scams [47:31-48:45].
• Transaction mechanics: details of structuring acquisitions, including offering cash vs. equity to technical co-founders.
• The importance of community, even for solo founders.

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Memorable Quotes

• On taking action:

  “Action produces information.” – Brian Dean (paraphrasing Paul Graham) [43:01]

• On finding fulfillment after financial success:

  “I needed to reread that chapter [Filling the Void]... I think that’s why I was seeking another startup project.” – Brian Dean [35:22] “Tennis has all of these things in one activity... Now I don’t have that same sense of wanting to start something new.” – Brian Dean [53:01]

• On winding paths to success:

  “As is nearly always the case, his path wasn’t a straight line... but a series of winding turns, all fed by experiments.” – Tim Ferriss [00:00]

• On learning from failure:

  “The first time didn’t scare me straight enough. So I went back... It didn’t work.” – Brian Dean [12:18]

• On life post-acquisition:

  “I was basically running on a treadmill and then I just hopped onto another treadmill that was right next to it and just kept going.” – Brian Dean [30:55]

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Notable Segments & Timestamps

• Brian’s rock-bottom & 4-Hour Workweek discovery: [03:16–05:23]
• SEO crash course, Panda update & lessons: [06:05–12:31]
• Dreamlining & financial “enough” in Asia: [10:48–11:26]
• The Backlinko “200 Ranking Factors” blog post breakthrough: [19:08–21:34]
• Acquisition due diligence headaches/advice: [23:44–29:24]
• Post-sale malaise and “filling the void”: [34:19–35:42, 50:20–54:30]
• Exploding Topics, content strategy, and data-driven content: [37:48–41:00]
• Action over analysis—book recommendations: [42:45–44:06]
• Cost of starting each company: [44:25–45:32]
• Navigating geoarbitrage and expat life: [47:31–48:45]

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Practical Takeaways

• Strictly action-oriented execution delivers more value than endless planning.
• Billable advice: Document contractor relationships from day one.
• Don’t chase trends—obsess about being the best source on specific, sought-after questions/statistics.
• When you automate your income or exit, proactively invest in non-work structure and purpose to stave off boredom or existential drift.
• Quality over quantity: “10x” content beats publishing volume.
• Lifestyle design is a moving target; what starts as “enough” may change as your experience and environment shift.

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Closing

Brian recommends subscribing to his YouTube channel (“Brian Dean”) and following him on LinkedIn (“Brian E Dean”). The episode closes with reminders to be kinder than necessary—to others and to yourself—and links to all referenced materials in the episode show notes.

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For anyone grappling with starting, automating, or exiting a business—or wondering what comes after the “hustle”—this episode provides not just strategies but hard-won wisdom about aligning your work, money, and fulfillment.

Transcript

[Tim Ferriss]

Hello boys and girls, ladies and germs. This is Tim Ferriss, and welcome to another episode of the Tim Ferriss Show. This is a shorter episode and by request, many of you have asked for more 4 hour workweek case studies. These are conversations with people who have read the book, applied it, and built lives and businesses that certainly I never could have imagined. Brian Dean is the focus of today's conversation, and his story starts exactly where a lot of great stories start. Broke, directionless and eating canned beef stew in his dad's basement during the 2008 financial crisis, he picked up a copy of the four hour workweek. He read it, which is not that uncommon, and then he took action, which is less common. As is nearly always the case, his path wasn't a straight line going from kind of bottom left of the graph to the top right, but a series of winding turns, all fed by experiments. And he has learned a lot. He has done a lot. Today's episode covers geoarbit, arbitrage, testing assumptions, cheaply building a muse, automating income, and also filling the void. That's a chapter that a lot of people skip over. His journey includes failures, two successful exits, and a hard won answer to the question that most people don't think to ask until it's kind of late in the game. What do you actually do with more time once you have it? Good problem to have, but quality problems can still be pretty gnarly if you don't think about them in advance. So before we get to the conversation, a little more on Brian. Brian Dean is the founder of Backlinko and Exploding Topics, both acquired by Semrush, which itself was recently acquired by Adobe for $1.9 billion. His work has reached millions of readers and has been featured in outlets like Forbes, Fast Company, Bloomberg, and the New York Times. You can find him on LinkedIn. Brian E. Dean that's B R I A N middle initial E. Last name Dean D E A N and you can find him on YouTube at Brian Dean. And last but not least, special thank you to Elaine Poffelt for getting Brian's story on my radar. Elaine is the author of the Million Dollar One Person Business and more recently, Tiny Business, Big Money. She is fantastic. You can also, if you want, search her name on Tim Blog and a couple of episodes that feature her will pop right up. So that all said, without further ado, please enjoy this four Hour Workweek case study with Brian Dean. At this altitude, I can run flat out for a half mile before my

[Tim Ferriss (Sponsor/Ad Reads)]

hands start sh I answer your Personal question.

[Tim Ferriss]

Now I've seen a perfect time.

[Tim Ferriss (Sponsor/Ad Reads)]

What if I did the opposite?

[Brian Dean]

I'm a cybernetic organism. Living tissue over metal endoscopy.

[Tim Ferriss]

Brian, nice to meet you finally. Thank you for taking the time.

[Brian Dean]

Hey, great to be here.

[Tim Ferriss]

Brian. Where should we begin? I'm thinking maybe because the impetus for this is somewhat around the connective tissue of the four hour work week. Should we just begin with how on earth you and the four hour work week intersected? Maybe we start there.

[Brian Dean]

So it intersected at a really weird and sort of low time in my life where I had started a PhD program at Purdue. And it was just overall not great experience. I went in gung ho. I'm going to be a scientist and all this stuff. And then the hard reality of pipetting in a lab and having an advisor breathing down your neck was like, I can't do this anymore. I'm out. So my plan was to get a job because I had a degree. I was like, let me get a job as a dietitian. Unfortunately, that didn't really work out and I ended up in my dad's basement.

[Tim Ferriss]

What was the timing of this? This was what year roughly?

[Brian Dean]

This was 2008. So I think the book was relatively new then.

[Tim Ferriss]

Yeah, 2008. That would have been a year after publication, let's just say. And also not exactly the hottest job market for people who may not recall. It was a tough time overall because of the financial crisis.

[Brian Dean]

Totally unbeknownst to me as a, you know, going to graduate school, spending most of my time at bars drinking, the great financial crisis was like, over my head. Never heard of it until I tried to get a job. And suddenly it became very real very fast. I was in my dad's basement, broke, no girlfriend, obviously no real prospects. Like, I'm just kind of lazily applying for jobs every morning and just sitting around and watching Jerry Springer in the afternoon. That's pretty much my day. And then one day I have an idea. I'm like, I should start something. I don't know where this came from. I'm like, I should start a search engine for nutrition questions. When people ask how much vitamin C is in a carrot, it'll just give them the answers. This is like basically what an LLM would do way before and someone that's not remotely qualified to come up with something like this. So I was like, how do I start a business? I had never crossed my mind before. I literally thought starting a business was like in the office when Michael Scott gives his lecture and he's like, first you need a building. So I'm thinking, this is this huge undertaking I'm about to do. So I go to the bookstore to find a book to help me get started. And I saw the four Hour Work Week, grabbed it, and it just sort

[Tim Ferriss]

of spoke to me what happened after that?

[Brian Dean]

I blew my mind. I read the book. I'm like, well, I could start a business. It was just a crazy, mind blowing concept that someone has no experience, was totally broke, could start something. Not necessarily be a smash hit, but you could start something. I just followed the book exactly as it was written. I literally had notes in the margins. You had those little Q&As at the end or little steps at the end. I would make sure I wouldn't go past that page until I did everything.

[Tim Ferriss]

Oh, God. My dream reader.

[Brian Dean]

I was like, I'm not gonna go to the next page until I'm ready. Good and ready. I followed the plan and then created an ebook about nutrition, how to help your back pain with nutrition.

[Tim Ferriss]

And we have so much to cover. I know I'm cheating a little bit. So I think it's fair to say that your first attempt did not turn into the mega hit that you might have hoped. Turns out it's hard to get traffic, or it can be hard to get traffic. And if you don't have a budget for paid ads, well, I guess necessity is the mother of invention, or at least learning. And I want to add a sidebar here, which is, this is so fucking common. It is incredibly common that you basically have your first love relationship, seldom works out, but you learn a lot and that leads to something else. But tell us about what you learned and how you adapted to that first experience.

[Brian Dean]

I spent all this time on creating a product that I thought was helpful, I thought was good. And then it was like, now what? You know, how do you get people to actually see this thing? And like you said, Tim, there's paid ads. Which wasn't really something that I could do considering I was broke in my dad's basement having Dinty Moore beef stew for dinner every night. Or so called free traffic. Which I was like, what? Free traffic? How does that work? So of course I went all in on that and eventually sort of stumbled on this thing called search engine optimization, which was like, you can rank in Google and people who are searching for what you sell, you can get in front of them. And I was like, oh, I use Google. And I never really understood that there was this whole world behind the scenes figuring out how it works. Trying to game the algorithm and stuff. And that sent me down the path of learning this thing called SEO.

[Tim Ferriss]

Also, I would say just to paint a picture for folks, because I remember looking at this when I started my first, let's call it real business. Also out of necessity, when everybody at the startup I joined got fired in 2000, 2001, not a great time for most.com companies. So I was working off of my soon to expire Cobra Healthcare in California and eating also microwave dinners. Or I remember I had a couple of favorites at Jack in the Box, which was in the parking lot of a Safeway. So that was my nutritional intake. Very similar, it sounds like, but slowly figuring out the mechanics behind these things that we use every day. And you took it certainly a lot further than I ever did. It's the wild west. SEO can be, especially those days, kind of the wild west. So you built up a huge portfolio of domains. It seems like something like close to 200 or over 200. What was the game plan when you started getting into SEO and then flashing forward, what was the plan in terms of revenue generation?

[Brian Dean]

The idea was you'd have these one page websites, rank and then you'd have AdSense display ads on each of those. And back then it was sort of a loophole that if you had a domain that matched the keyword exactly, then it was a massive advantage in the search results. I would have like L' Oreal Shampoo.org and I would just write like a thousand words about why l' Oreal Shampoo is great, which I obviously don't really know a lot about. And for those who can't see the

[Tim Ferriss]

video, we are both completely bald. Yeah.

[Brian Dean]

And yeah, putting AdSense ads on the pages times 200. And the idea is that you scale up enough and take a few steps later you got a private island or something. You're right.

[Tim Ferriss]

ABC M and then Private island.

[Brian Dean]

So.

[Tim Ferriss]

So let's backstep for a second because we can talk about the business and the business experiments and adventures, which we will, and misadventures, AKA Panda death, which we'll probably get to. But if we're looking back to your reading of the book, there are a couple of different directions as a chooser and adventure map that you can take. And part of that oftentimes is figuring out your target monthly income, doing exercises like dreamlining, which people can find for free, to figure out exactly what it is that you are building as a lifestyle and the things you want to do, et cetera. And you come up with this very Precise, not necessarily accurate, but it's a starting point number. Where were you when you're going through all of this? Because you can build a business for the sake of building a business and generating all this cash. But then the question is, what do you do with that? Right. How does it inform your life? Were you thinking about that stuff at the time or was it just get out of the basement and eat something?

[Brian Dean]

Yeah, it was get out of the basement, have a proper meal. Exactly. Have a meal that's not out of a can. I just wrote that and the whole dreamlighting section, that was basically what I wrote. It morphed a little bit. At first it was that and then building the 200 websites. At some point I was in Asia backpacking and then my whole world changed to 3K a month. I was like, if you can get 3K a month in Thailand, you can live like a king. So my whole goal just became to get 3k a month passive income. That was like my entire focus. So it sort of shifted. Once I had sort of a lifestyle that I tried and liked. I was like, I could live like a backpacker, I can do this. So then it just became 3k a month for a long time. For like a year.

[Tim Ferriss]

For a year. Did you hit the 3K a month before the Google slap, which may be one and the same as the Panda update? I'm not sure. Maybe those are two separate things entirely. But where were you before things got pretty strongly corrected?

[Brian Dean]

Yeah, I was maybe at 3k a month around there for like a couple months, had a good ride and then it kind of got slapped. Didn't last long. The first was a Panda update as you mentioned, which was a very content focused update.

[Tim Ferriss]

By Google.

[Brian Dean]

By Google. It was an update that basically was if your content is thin or repetitive or not helpful, we're going to wipe you out. And it was like a one day they push a button and you know, thousands of websites got completely obliterated, including mine.

[Tim Ferriss]

That's a rough. Where were you when this happened? Do you remember when you got the news?

[Brian Dean]

I got slapped twice. The first time didn't scare me straight enough. So I went back to the. I was like, oh, I'll just do a different type of black hat SEO and I'll get away with it. It didn't work. So that one, I think I was in Thailand when it happened.

[Tim Ferriss]

Let's then go to. You get scared straight, as you put it and you build your first, as I think you've put it, real site, which isn't l' orealshampoo.org, it's something else. When you decided to hop to the white hat side of things, what did you end up doing and why?

[Brian Dean]

There was that first update and then a second update where I was in Spain in Granada, and I went to my hostel. I checked the laptop and it was like, again, it was like a repeat of the Thailand experience. Everything dropped. This was a different set of websites that got knocked out. And I was like, you know what? This is crazy. Why am I doing this? This is an insane way to live. So then I was like, I'm going to build this one real website. And I was kind of inspired because there were these forums at the time with these marketing people, and they're like, spam, spam, spam. And there was always a. There are a couple voices in there of people who were like, build a real business. What are you guys doing? Build something real that's durable, that's not 100% reliant on Google. And I kind of ignored those people. And then once I got hit that second time, I was like, okay, it's time to build something real. So I built a sort of real site in the personal finance space, wrote real blog content, didn't do any shady spammy stuff, and tried to keep it on the up and up.

[Tim Ferriss]

What is the bridge or what happens between that and then building Backlinko? How do you end up segueing? I mean, I guess this could be like a very fast montage in the sort of fictionalized movie of your life. But what happened to go from there to Backlinko, which ultimately you ended up getting acquired? What transpired between those two?

[Brian Dean]

So once this site started to get a little bit of traction, I was like, wow, this is a whole world. I didn't know about real marketing. Why SEO? And it was fun, it was working, and it was more enjoyable because I didn't have to look over my shoulder that I was going to get hit with an update next week. And it was cool because I'm reaching out to other websites and like, oh, this is really helpful. And they're linking to me. I'm not paying for links. They're just naturally doing it. And I'm like, how do I learn more about this? This whole world opened up. I'm like, how do I get better at this? And all the advice that I read on all these white hat SEO blogs were vague advice. Create great content, build relationships with other

[Tim Ferriss]

people, market your site, lead with integrity. You're like, okay, what's my next step very unclear.

[Brian Dean]

Exactly. It was as vague as you can imagine.

[Tim Ferriss (Sponsor/Ad Reads)]

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[Tim Ferriss]

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[Tim Ferriss]

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[Tim Ferriss (Sponsor/Ad Reads)]

Tim.

[Tim Ferriss]

Then Backlinko is a case of sort of creating the thing that you couldn't find. Is that, I guess a fair way to put it?

[Brian Dean]

Yep.

[Tim Ferriss]

One thing that I saw here in the prep notes, which I was like, oh, that's so smart, and I wanted to highlight it, is there are a number of things, obviously that you ended up doing really well, that seem to have set the stage for a lot of things that came. One of them was digging through Google patents and engineer statements. And I'll come back and sort of expand on why this is smart, but it'll probably become very obvious once you explain why you did it. Why were you digging through Google patents and engineer statements? Are those part of the patents or are those something separate?

[Brian Dean]

Separate.

[Tim Ferriss]

Okay, so could you explain what you were doing?

[Brian Dean]

When I launched Backlinko, I was like, there must be other people like me who are getting into this whole world of Yhasio. They want to learn more about it and they're disappointed about what's out there. And it turned out there was. I just didn't know how to reach them at first. So I followed the same advice that I read for starting a blog, which was you need to publish every week or every other day. And that's how you build an audience. You just publish and pray that people come. So that's what I did.

[Tim Ferriss]

People still give that advice. Publish and pray. Yeah, exactly.

[Brian Dean]

So yeah, I did that and banged my head against the wall and I was like, you know what? I came up with an actually creative idea for a post that would be really special instead of just the stuff I was putting out every week, which was good. It was definitely actually decent to give myself some credit. But it wasn't anything that's going to grab you by the shirt and be like, I need to read this. It was just slightly above average what was out there. I was really going on that consistency play. If I do this consistently over time, there'll be a secret society that will just send me traffic as a reward for being so consistent. I didn't really have the whole thing planned out, to be honest. I just thought I just knew consistency equaled traffic at some point and it honestly didn't for me. So I Had this idea for a post which was Google recently had said that there's 200 ranking factors in the algorithm. So I was like, let's just try to find them. Obviously a lot of it's going to be conjecture and guessing and speculation, but let's just do a list of 200 instead of the list of 10 or 20 that I'd seen out there. And then I got to like 55 and I'm like, man, you have to really dig to find some of these. And that's when I went through the Google patents. And also people would interview Google engineers or they would give statements about. They'd be at a conference and they would give a talk and you know, one of the slides would mention a ranking factor that they're considering. So it took a lot of digging. It took like 20 to 25 hours to complete this single post. And that's really why I was digging into all this stuff.

[Tim Ferriss]

I just want to add an addendum to that, which is people who have not heard of this approach. For some folks, they'll be like, I or someone else has done that. But it is incredible what you can learn through reviewing patents and looking at very niche events, industry events, for videos and transcripts of presentations. This was incredibly valuable when I was getting started as well. Mostly looking at closed door or very small event presentations and things like that. All right, so that was sort of a massive post that you really invested in. 25 hours, not trivial. That's a lot more presumably than you're putting into the kind of publish and pray consistent approach to just sliding a plate with content salad out the door and hoping that leprechaun is going to show up and trade for a pot of gold. Right, so what was the response to that post?

[Brian Dean]

Massive traffic and controversy. Kind of everything you want in a piece of content, to be honest. I mean, you had the traffic, you had people, the wow factor and then you had the controversy, which is like, Those aren't Google's 200 ranking factors. No one knows those. And then people saying, well, this is at least trying to come up with something. And then people saying, well, it shouldn't do it. So it was like perfect little debate around it. That was pretty lightweight. It's not anything super controversial, but just enough to get people's attention. So yeah, brought in, I would say I was probably getting 150 visitors a month. That probably brought in a couple thousand when I first put it out. It's brought in millions since then.

[Tim Ferriss]

What did you then follow that up with in terms of lessons learned, coming up with new rules for yourself in terms of how you were going to approach the business. How did that inform things going forward once you saw that response?

[Brian Dean]

I just threw out the whole playbook. I was doing consistency thing. I would even have on Fridays I would have a Q and A. I would just put five questions and answer them. And of course I wasn't getting any questions, so I just completely made them up and then answer my own questions just to have something to put out there. And I'm reading it, I'm like, why would anyone want to read this? So then I just scrapped the whole thing and was like, I'm just going to put out something once a month and it's going to be the best thing on that topic that's ever been written by 10x. And that was sort of how I totally changed my content focus to quality over quantity.

[Tim Ferriss]

You had a fun YouTube video on ultimately the acquisition of Backlinko. And I guess the original email you got was like, hey, we'd love to connect, to collaborate. And you're like, well, that smells like every bullshit spam email I've ever received. So you just ignored it, right? Yep, as I remember. And we won't spend a ton of time on but what is Semrush? This is the acquirer, ultimately. But for people who don't know what is Semrush?

[Brian Dean]

They're a marketing platform that help you get better results from SEO, pay per click, and also now AI search.

[Tim Ferriss]

Are they private, publicly traded? They're publicly traded, right? Yeah.

[Brian Dean]

It looks like they got acquired by Adobe last year. So they will be part of Adobe, I think sometime this year when everything goes through.

[Tim Ferriss]

Got it. And they acquired you ultimately while they were public. I mean, there's so many good aspects to this. Do you want to tell the story about flying to Boston? I mean, eventually this contact, I can't remember his name, but since you ignored the first email he wrote and basically said, hey, look, we might be interested in buying your company. Let me be direct. And you're like, okay, I'll reply to that one. But can you tell the story of flying to Boston? I think it's pretty funny. I also liked in your video and you said up to that point I hadn't sold anything except for maybe a used car. I think you said something like that. I was like, that's a pretty good line. Okay, so the first Boston trip, what happens there? What's in your mind?

[Brian Dean]

In my mind, I'm like, we're going to close this thing let's go to Boston. It was really a meet and greet where the executive team just wanted to meet me and chat about how it could help them, how Banklinko could fit into their platform and their business. So I spend the day with them in the office, and then afterwards, we all go out to drinks to celebrate the deal. And I'm like, shitting myself, right? I'm like, what? We're celebrating the deal now? Like, I never saw a contract or an agreement or anything. I'm like, we're gonna sign it, like, tonight. So we go out and we're at Legal Seafood in the Prudential center taking shots. Yeah, this is great, Brian. This is gonna be the best thing ever. And I'm thinking, where's the contract? When are we going to sign? I really thought right there, they're going to. Did I miss something? Did I black out? Exactly. I'm like, did I agree? Is a verbal agreement enough for a deal like this? So, yeah, that was definitely. I was way off on that. It took two more months of due diligence after that meeting, the deal, to actually close.

[Tim Ferriss]

You said two months.

[Brian Dean]

Yeah.

[Tim Ferriss]

Which for people who have never gone through it can be very challenging. If you don't have your ducks in a row, which almost nobody does unless they've been through this before or are venture backed and they have of people overseeing all this stuff. Two months is pretty good. It's painful, but, man, due diligence can go on forever for people who are starting a company. Maybe they never intend to sell it, but, hey, you had not gone into Backlinko thinking that you were going to sell it. But they want to preserve the optionality. I remember coming across, and I haven't read it in a long time, but a book by John Warrilow called Built to Sell, which talks a bit about this, and I thought it was actually very good. Like a very. I don't want to say basic, but pretty sort of foundational primer for some of this stuff. But what advice would you give to folks? I mean, one comes to mind, which I have also had to learn the hard way about independent contractors. But what are some of the tenets or sort of commandments of like, hey, just in case one day you want to sell this thing, Here are a couple of things that I learned. Anything come to mind?

[Brian Dean]

Independent contractors, for sure. Maybe you can expand on that sim, because you have experience with that.

[Tim Ferriss]

If you ever want to sell something, the acquiring party is going to want to know with some assurance, and they'll have reps and warranties in the agreement that basically say, hey, if you miss something or you're not telling us the truth, there's going to be a world of trouble and we'll probably be able to back out of the deal and take all the money back. But they want to know that everything they're buying is free and clear. So if you've had as I have and as you have in some cases, well, I'll just speak personally. Always maintain a very small full time team, but have used dozens and probably hundreds, certainly hundreds of contractors over the span of decades. And if you're building something and they want to see they meaning the acquiring company, every single contract to make sure that someone isn't going to come out of the woodwork and say, hey, I own a part of that. Hey, I contributed this and therefore I am entitled to a piece of equity, yada yada, yada, yada, which if the deal's big enough, come out of the woodwork no matter what. You see this with a lot of tech IPOs and stuff. As soon as they file the S1 getting ready to IPO, then some rando comes out of the woodwork and says I'm the seventh co founder and you're like what? No one's ever heard of this person and they just want nuisance money to go away. That's the relatively short and sweet on independent contractors. This is going to be true also with pretty much any agreement or contract. You just want to document, document, document, make everything formal, no verbal, no handshake. If you want to preserve the option to cleanly and hopefully relatively quickly sell a company later. Anything else that you would add to

[Brian Dean]

that, Brian, if you don't have your finances in order, like you don't get P and ls, that is something they obviously will care a lot about. And luckily I had a good accountant that did that stuff, so that wasn't a big deal. The number one time sink for me was the independent contractors. I mean I'm like you. I hired so many people that created a blog post image or something or a social media image once for like 10 bucks and I had to go try to find them. Have to hire almost like a private investigator to find these people because you don't even barely remember them. Even people that ghosted me. I had people that I paid a deposit for work and they never even replied. They totally ghosted me and I still had to reach out to those people. Of course they're not going to reply, but you have to show that you tried and then Obviously, since this experience, every contractor that gets hired signs an ironclad agreement that says you don't own any of this work once you're paid, it's a property of blah, blah, blah. That made things a lot easier the second time. But I had no idea this independent contractor thing was so important to the acquirer. But it absolutely is.

[Tim Ferriss]

Yeah. So we won't spend a ton of time on what followed. But there was one funny anecdote about the public announcement. Could you just explain that? Given the time zone differences, I thought that one was great.

[Brian Dean]

Time zone differences and I'm early to bed kind of person. So they told me that, hey, Brian, we're going to announce this tomorrow and we're going to announce it at 5pm Eastern. And I'm like, oh man, I don't know. Is it possible to send it earlier? That's like 10pm here. I'm already kind of getting ready for bed, basically saying I'm in my PJs at that point. Is it possible to push this earlier? And they said no, because it's a public company due to SEC rules, we have to make these announcements after the markets close. Yeah, I was so embarrassed. I was like, oh, yeah, right. I forgot the league I'm playing in here.

[Tim Ferriss]

So you sell the company, presumably there's some type of earnout or period of time for which you're required to still work on Backlinko. Who knows what the exact terms are of that. But for people who've never gone through it, you can have a vesting period, you can have an earn out where you get X percentage of the total purchase price based on hitting or exceeding X, Y and Z metrics or whatever. So there's a period of time like that post acquisition, let's just say, because I know that was very stressful and you started grinding your teeth and that kind of evaporated as soon as the deal was done. Let's just flash forward two or three months after the acquisition. What does your life look like? What does a week look like for you?

[Brian Dean]

It's honestly not that different because I had another startup that I was already working on. I was basically running on a treadmill and then I just hopped onto another treadmill that was right next to it and just kept going. So there wasn't a whole lot of downtime to really reflect or analyze that one day that the announcement was made, especially the next day because it was late here. So the next day was really when I was sending messages to people and stuff and getting congratulations and whatnot but after that day, I was pretty much back working on the next thing. Didn't reflect too much on it. So my life was more or less the same. One day, after

[Tim Ferriss]

looking back, are you basically like, hey, I'm a border collie. I need to work or I'm going to go crazy. So I'm glad I did that. Do you wish you had approached it differently?

[Brian Dean]

I kind of wish I approached it differently, yeah. And looking back, I wish I took some time off. It's just tricky because you know how it is when you have a startup. It's kind of a strange situation. Like, I had a new company that was growing. I had this old company that I sold, and it felt weird to say to the new team, like, hey, guys, I need to reflect about how great my life is. I need to chill out. You guys still work, though. Like, you work your asses off. I'm gonna sit on the beach for a while. So it felt a little weird. I felt like I kind of had to go back into the trenches with them right away, almost even more so to prove, like, look, I'm not done. Like, I'm not going to rest on my laurels. We're still in it to win it.

[Tim Ferriss]

And financially, at that point, were you focused on the new company, exploding topics because you wanted to get to that sort of big pot of gold at the end of the rainbow? Like, what was the driver behind that? I don't know to what extent you were sort of financially stable, had savings. We don't have to get into all the nitty gritty if you don't want to. But I'm just curious, what was driving the involvement in the new company for you?

[Brian Dean]

It wasn't really 100% financial. When I sold Backlinko before then, I was probably okay for most of my life. Then when I sold Backlinko, it was like, okay, I'm probably good for forever. And then I wouldn't have probably started something else right away if I hadn't already. Towards the end of Backlinko's, when I was involved with it before I sold, I was honestly getting a little bit bored with it. I was bored talking about the same things, writing about the same things, doing the whole course launch thing. And I kind of wanted something new. And I saw an opportunity where there were more trends than ever and I couldn't find a good tool for curating them that was like, here are all the trends in this space right now. There was Google trends, which is fantastic. If you know about a topic and you want to see how it's trending. But what about a trend you've never even heard of? And that's sort of where I realized the opportunity was. So it wasn't really purely financial. It was more like, this is kind of exciting and new. I think it's a good opportunity as well. And it'll give me something to do between these sessions with Backlinko, which was. It was also boring because it was so optimized. I work three hours a week. It was like four hour work week. Honestly, at the end, it was getting so much traffic on autopilot. The launches were really easy to do. Even courses were easier to create at the end because it just had it all down to a science. Even if it was a totally different topic. I knew exactly how to create a course. So the challenge wasn't really there. And this was like, okay, new challenge, new space. It wasn't so much financial. It was more just to freshen things up and to try something new.

[Tim Ferriss]

Yeah. And you'd also already committed to other people with this new startup, so it makes a lot of sense. When you had with Backlink go so much on autopilot, the three hours per week, what were you doing with the rest of that time? Because the most. And we don't have to dig into the book too much here, but if I had to point to one chapter that people pay no attention to because typically they're like, oh, yeah, that'd be a nice problem to have. And they forget about it. Is the Filling the void chapter. Filling the Void chapter. The four hour work week is really important. So you don't go into psychological freefall, among other reasons. But what were you doing with the rest of your time? If Backlinko, at one point, when the flywheel was really spinning, was only occupying or requiring three hours a week, I was bored.

[Brian Dean]

Honestly, I wasn't feeling it. Well, I wasn't filling the void. Going to the gym, reading books, playing video games. I think that was part of this. And we. This boredom was. I needed to reread that chapter essentially and fill this with something meaningful. And I think that's why I was seeking another startup project.

[Tim Ferriss]

Because I'm like, yeah, 100%.

[Brian Dean]

It was like, I need to work, I need to build something. I'm not building this, I'm just maintaining it. So that's really what got me into exploring topics. So honestly, the filling the void chapter, the whole filling the void concept, I really only took seriously recently. But before then, I've filled it with sort of nonsense to be Honest. And then started another startup.

[Tim Ferriss]

What were some of the things you did differently with exploding topics? After all the experience with Backlinko, and maybe things that in retrospect, you're like, wow, that was a really smart decision. And change. And maybe somewhere you're like, okay, lesson learned. Would probably. If I were starting from scratch with exploring topics, I would have done it differently. Anything come to mind in terms of good and bad decisions?

[Brian Dean]

Yeah, we can start with the bad one, which was how to monetize. This site had this very strange idea that we're going to create this awesome free resource that anyone can visit and just see trends right away. They can filter, they can go by category. And you think, oh, how are you going to monetize that? Logically, you think SaaS, an upgraded version of what they're seeing for free. And for some reason, I was like, a paid newsletter. Like, let's create a paid newsletter. So we created this paid newsletter that was granted helpful in, like, objective terms, but not necessarily for that person who wants to see trends in their particular niche. So we would send them a trend on, like, some sort of face cream and then on, like, a car and then a battery and then a tech startup. And they would be like, what is this? People were like, I want just trends about E commerce. I just want trends about this one thing. Like, why are you sending me all this stuff? And then people would also sign up thinking it's SaaS. Even though we said everywhere, like, paid newsletter, paid newsletter. And they'd be like, I thought this was SaaS. I thought this was SaaS. That was our number one complaint. And, yeah, sometimes you just need to get that beating over your head. Because I was like, oh, SaaS is so complicated. My co founder was a coder. But I'm still like, oh, we're gonna have to hire developers. And I don't know anything about this whole world.

[Tim Ferriss]

And for people who may be listening, who don't recognize the term, a lot of people will. But software as a service? Think about Dropbox. Maybe not the best example, but Dropbox is a great example. But with a lot of these products, there's a freemium version, there's a version that you get to use for free. And then if you want a bunch of additional storage or features or access, whatever it might be, then you pay 9.99amonth or whatever. And there's like the basic intermediate, advanced version, enterprise, et cetera. That's SaaS. Sorry to interrupt. I just wanted to define that.

[Brian Dean]

If you had told me that before we started, I would have been like, oh, logically then we should have the premium advanced enterprise version in the backend instead of the paid newsletter idea. So that didn't really go well until we ultimately shifted to what we should have been in the first place. So that was sort of the bad decision. The good decision was definitely investing in this data, publishing data early on. So with Backlinko, this is something I only discovered after like five years of running the site and then with exploring topics, I was like, day one, we're going to publish tons of data, we're going to be the source. That's another strategy, like be the source of information on technology, software, e commerce trends, anything trend related, we are going to be the source. We're going to have the latest data, we're going to have the best visuals and we're just going to be the source for that information. As opposed to writing how to content, we really focus on data driven content.

[Tim Ferriss]

Did it work right out of the gate or was there a formula that you realized worked after you had a particular well received publication of data?

[Brian Dean]

It took a while to get going. A lot of mistakes, a lot of posts that weren't great or the topic wasn't a good choice. What really helped us, what was sort of the smash hit, were these very specific stats that people look for. So what I discovered through this process was this stats page idea is nothing new. People write the biggest stats around the fitness industry or LinkedIn stats or whatever, and those are fine. But usually journalists aren't looking for LinkedIn stats or TikTok stats. Some of them are and that's fine. But most of them look at something very specific, like how many users did TikTok have? Or how many people use LinkedIn every day like daily active users. Or how many posts are on LinkedIn every day, like it's super specific. So if you're able to find a credible stat around that, then you can crush it even if you're not the one that developed it. A lot of times these are also buried in PDFs or white papers or again interviews that you have to pull out. One of our biggest smash hits in this area was how many users does ChatGPT have? Granted we publish this early. That's another thing that can help a lot. If you publish one of the first or the first specific stats page, then you get into this virtuous cycle where you're very visible when someone's searching for that topic. Then they link to you, they mention you, makes you more visible, and then you just are like in this massive flywheel. So one of our best pieces was how many users does ChatGPT have? And every once in a while Sam Altman will give a talk and he'll mention it, or when they raise a round, they'll mention it. And all we did was just document their user growth based on these statements that they made. The initial post probably cost hiring a freelancer like 200 bucks. And then to update it every couple months, it was like another 50. And it's been referenced like 3,000 times. It's absolutely insane. The effort to reward ratio is nuts on that. And of course it's just like part of it is some pieces do better than others. But we've noticed that that formula tends to work well. If you can find a trending specific stat that bloggers or journalists are looking for when they write about that topic, they're very likely to reference you.

[Tim Ferriss]

So I read. I'll give credit here. This is on growthmanifesto.com found this doing research. You were interviewed towards the end of that interview by Alex. He asked you what the best piece of business advice was that you've ever received. Now, this may have changed and there's probably more, but it was Noah Kagan advising you to double down on what works. Could you expand on that? And then I'm wondering if there are any other mantras or short pieces of advice that you would also put on the Mount Rushmore of your best advice that you've received.

[Brian Dean]

It sounds so simple, but it's one of those pieces of advice that's simple but hard to follow. Because when you're running a business, there's like a million things to worry about to focus on. There's new opportunities, new challenges, other competitors. You have an employee that's sick. It's hard to really focus on that little thing that works. I think this is especially important when you're first starting out, because when you're first starting out, nothing's working. Almost by definition, you're starting something new. At least in my experience, when I'm starting something new, I don't know, like nothing's working. And then when something does, most people are like, okay, that works, now let's go something else. But instead you should just take that niche. It's almost like a little niche. When you're rock climbing, just take that niche and just double down, triple down, quadruple. It should really be like 10x down on what works. Because it's so rare that you find something that works. And honestly, in most businesses, if you can find one thing that works and scale it up. That can get you pretty far.

[Tim Ferriss]

Aside from the four Hour Workweek, which was. This was a catalyst of sorts in the beginning. Have there been any other books that stand out or resources? When someone comes to you and they're like, I'm thinking about starting a business, I'd like to start a business. Are there any books or resources that you tend to recommend? Frequently?

[Brian Dean]

Yes. For people that are just like, I want to start a business. And they're like, I don't know what to do, how to do it. They're totally green. Then Ready, Fire, Aim is usually the book that I recommend. You familiar with that one?

[Tim Ferriss]

I've heard of it.

[Brian Dean]

Michael Masterson.

[Tim Ferriss]

What leads you to recommend this book?

[Brian Dean]

It gets people into the action mindset, like leaning towards action instead of analysis. I was guilty of this when I first started doing a lot of spreadsheets and analysis and business cards, registering a company, all those things that you can do later that don't really matter. This gets you going on the most important things and then later you can always change course. But the key is really starting, starting, starting. Or like Paul Graham says, action produces information. So this book will hopefully give people a kick in the butt to get started. Instead of analyzing and then being like, okay, now I'm ready. Just be like, start today and then change as you go. I feel like that book is almost a litmus test. If you read that book and at the end you don't do anything, then you're probably not ready. Yeah, the whole point is to get started and it gives you advice on how to know you've got traction and what to do once you're traction. So I feel like if you just read the book and you're like, okay, what's the next book to read? It's probably not the best approach. So that book is hopefully the kick in the butt that someone needs.

[Tim Ferriss]

This might be a tough question to answer, but how would you define the startup costs for Backlinko and Exploding Topics in the first three months of those two companies existing, how much money was invested in each of those? How much money was required invested?

[Brian Dean]

For Backlinko's case, a few hundred bucks at the most. It was like domain WordPress. I probably hired someone to create a basic blog Design theme for WordPress. Don't remember how much, but if I spent a thousand, I'd say that's a lot. I was probably more like 500 bucks. Because it's a blog. I mean, really, at the end of the day, There shouldn't be a lot of cost involved with that. Exploring Tabby's a lot different because I acquired like a prototype version from someone for 75,000 to start with. That was part of their pay package as well. So just on day one, I was in with that much. And then it was a redesign and a rebrand, adding more trends, hiring a couple people to do some basic things. So that was probably more like 90,000 something in that range. But it was a unique situation because it wasn't built from scratch. It was acquiring someone and then that was also paying for some of their time. It was kind of like hiring them as part of the acquisition. And that was paid out over the course of a few months. So I'm not exactly sure how much would be like in that first couple months, but it was in that range.

[Tim Ferriss]

Why did you acquire something and what was the deal structure of the acquisition?

[Brian Dean]

I acquired it because I was trying to build this exact thing myself and just stumbling and stubbing my toe over and over again. So I knew that there was an opportunity for this trend. I couldn't even describe it very well. It was just, you want to go to a website and it just shows you trends in whatever niche you're interested in. And that sounds so simple. But nothing existed like that, believe it or not. And I hired someone to build something like that and it was horrible. They used Reddit, so we'd look at subreddits and we would see how many times a word was mentioned or something. We found nothing valuable. The signal to noise ratio was completely backwards. It was like for every 200 hits, one was decent. And then one day someone forwarded me this random site, this guy started and I'm like, no, this, this is exactly what I want. But it was even better than I had imagined. So then I reached out to him and then the deal structure was buy it 100% straight up. Part of the acquisition cost will be, you'll get paid that. And then on top of that, if it goes well over the first, I think, couple months, then we can set up some sort of part time deal and if that goes well, we can do full time.

[Tim Ferriss]

And he would be helping you with throughout that entire period of time to determine, help you determine if it's going well or not.

[Brian Dean]

Exactly. And he was the coder and developer behind the original version, so he was best qualified to continue to work on it and improve it rather than hiring someone random to come in. It was his vision to start with. Then I said, if it goes well with full Time for I think another month or so we'll be co founders on this thing. The only rub will be if you line up a lot of equity, then you're going to have to put money in to fund this thing. Or if you prefer that you get more cash, then you can just get a proper salary and then I'll own most of the business. So that's what we did. He chose more money and then he owned a part of as equity.

[Tim Ferriss]

How did you end up in Europe?

[Brian Dean]

Love, to be honest.

[Tim Ferriss]

Yeah, that'll do it.

[Brian Dean]

Yeah. I mean my wife, we met in Thailand many years ago and then we moved to Berlin. This is actually a funny story partially from the four hour work week, because you mentioned Berlin as this cheap place. So we're in Thailand looking at credit Craigslist and looking at all these apartments that are like palaces for €300amonth and we're like, Tim was right, this is amazing. You can live like a king in Berlin for nothing. So as we're flying there, we send out all these emails like we're going. And of course they're all scams. It's like, I'm lost and oh, I'm out of town, but if I lost my passport. But if you leave this money into Western Union, we show up to Berlin, we're in a hostel for €8 a night in a 12 bed hostel. While we realized that this whole thing, all these ads we're applying to is a scam. No one uses Craigslist in Germany. So then we eventually found an apartment, lived in Germany and she's Portuguese. So we visited Portugal a number of times when we lived there and eventually was like, we could freeze our asses off or we could live in the sun. So let's look at the sun.

[Tim Ferriss]

That's how we ended up here. The thing about the four hour workweek, right, the principles and frameworks all still work. Obviously some of the tech tools since they were Last updated in 2009, most of them are completely irrelevant. Probably not going to use GoToMyPC at this point to access your home computer remotely to do the work you need to do. But the pricing examples obviously have changed since it was first written in 2007, 2009. So the principle, the idea of geo arbitrage and applying that to what you earn and how you pay contractors, employees and then your living expenses, it applies, but definitely for anybody who ends up picking it up. If you read that doing something in Buenos Aires costs A, B and C, I would go online and fact check that because it's probably changed a little bit. But looking at all the questions I could possibly ask, I mean, what are other lessons learned or things that you would like to share with folks? Could be about your journey, could be about mistakes along the way, really. Anything at all. Because part of the value of these conversations is that we can get into a lot of specifics that are omitted in the magazine. Profiles of people that end up reading a list of highlights. And there's obviously a survivorship bias to begin with if people appear on magazine covers. I know that's an antiquated example to use, but what else would you like to share with folks or anything else you'd like to add just about the journey? Because it's not over. It still goes.

[Brian Dean]

One thing was honestly that I've discovered recently that I wanted to share would be actually filling the void. I felt the void after selling exploring topics and how I was able to fill the void.

[Tim Ferriss]

Yeah, please.

[Brian Dean]

So set the stage for you. I sold Backlinko and then about two years later sold exploding topics. And we're just kind of going full time, not super crazy, working all the time because I was fairly efficient but still working all the time and then went from that to stop to zero. And a lot of people, I think they have this feeling of listlessness, no direction, maybe a bit of depression. For me, the symptom was stress. I think I was wired for stress, not only just in general, but also because of the sale process is stressful. And then just because the sale is done, your body and I think part of your reptilian brain doesn't really recognize that. And it's looking for threats and it's looking for opportunities and it's just not chilled out. So I struggled for like two months with stress on my Oura ring. My stress was like 2x baseline from after I sold. And you'd think it'd be the opposite. You'd be like, this is great. I sold two companies, I'm good for the rest of my life. What is there to be stressed about? And then I realized what I needed was a hard reset. That was the first step. We went on a trip, got away from the environment, got away from the day to day life. And then it somehow was able to hack my brain to be like, okay, you're safe. Or like things are chill now. So when I went back home, the stress was gone. It was like back to baseline or below baseline.

[Tim Ferriss]

What was the trip?

[Brian Dean]

It was a trip to the south of Portugal. To the Algarve. Yeah.

[Tim Ferriss]

So went to the beach Nice oranges?

[Brian Dean]

Yeah. Toasted? Yeah. Good orange. Good oranges, yeah. Yeah. So spent some time down there, and that was just like the hard reset. I think it's just gonna get out of your environment. But then when I got back, it was like, stress is gone. But now feeling a little bit bored. Like that boredom was coming back, and I was tempted to start another startup. And I read this. Someone sent me this. Who? Another friend who had a big acquisition. He sent me this thing by. I think it was Harvard Business Review. And it was. They interviewed founders that had just exited, and they asked him their advice. What was it like? What were the good ups and the downs? And they basically said, when you sell, there are psychological dangers that can occur. One is that you lose your sense of structure. The other is you lose your sense of purpose and you lose your sense of connection with your team. It all goes away. You have it, and then one day you literally don't. So different people react to it in different ways. But they warn that a lot of case studies in this paper were saying people that started companies within a year of selling usually regretted it. Take a year and don't make any major commitments whatsoever. So that's what I did. It kept me from starting these. I had all these ideas. I'm going to start a subgroup, and then I'd be like a wait a year, wait a year, wait a year. And then by the time a year came around, I didn't really want to because I was able to fill the void largely with tennis. For me, tennis has been. It just one activity, fills almost all of these. Checks all the boxes and fills this void. It's amazing, man, because if you think about it, if you want to have fun, you play video games or watch TV or something. If you want to socialize, you go out drinking. If you want to exercise, you go to the gym. If you want to get fresh air, you go for a walk. Tennis has all of these things in one activity. And if you want a community, you need to. Actually don't even know how to do that outside of tennis. That was the thing that changed, was I joined a tennis club, and there's a lot of other entrepreneurs there, a lot of Americans, man. It's like the 51st state over there. To be honest, it's getting a little crazy. But anyway, so I filled the void with this community of people that are playing tennis, trying to improve, obsessed with the game, watching YouTube videos, reading about it, practicing all the time. And now I don't have that same sense of wanting to start Something new.

[Tim Ferriss]

I love that. And just a few observations since as you would imagine, since the book came out in 2007, I've had the opportunity to vicariously watch a lot of people grapple with this. And having worked with so many startups in angel investing, granted in a kind of venture backed environment. But a lot of the challenges are the same whether you're coming out of, for instance, I know guys in special operations, if you're coming out of running a company, if you're coming out of starting and running a company, when you lose, as you put it, and I really liked the categories you mentioned. When you lose the structure, when you lose in a sense the identity, when you lose the connection to team, you can end up with a severe degree of vertigo and a very precarious paradox of choice and something like tennis. And some people listening might think what tennis probably even if it's not the forever solution and the end all be all. What it does, just like getting your recommended daily allowance of essential amino acids and vitamins and so on, you're getting just enough that it provides you with the psycho emotional health and space to think about things more clearly instead of being reactive. You know what I mean? You're getting enough of all of those things and it provides you with a buffer and a certain equilibrium that allows you to think about things more clearly. And furthermore, this is not necessarily a problem you have to solve after everything vanishes. You can think about this in advance and experiment with things so that when you have a real phase shift, which in the context of the four hour workweek isn't necessarily selling a company, it's just like once you get it to a high degree of automation where it requires two, three hours a week, if that to manage, which is more common than people might think, what you do with the rest of the time is a tremendously big question. So I love that. Makes me want to go back to the Algarve. Also can get a little toasty.

[Brian Dean]

Could be worse, let's put it that way.

[Tim Ferriss]

Yeah, it's a good country for tennis. If it's possible for you to find that Harvard Business School piece, that HBS piece. Would love to put it in the show notes. I am sure that we can track it down one way or the other. But we'll put that in the show notes for folks who want to check it out.

[Brian Dean]

Yeah, it's a great read. It might have been Yale or something. I'll find it.

[Tim Ferriss]

Yeah, I know. Whoever it was. Brian, this has been super fun. Where would you like people to find you online, if anywhere.

[Brian Dean]

Let's start with YouTube. So that would be the first place. And then LinkedIn, Ryan Dean on YouTube and Ryan Edean on LinkedIn. That other person, he must have grabbed that one. I don't know.

[Tim Ferriss]

Brian, is there anything else you would like to say before we wind to a close?

[Brian Dean]

This has been great. Yeah, that's it.

[Tim Ferriss]

Thanks man. I know it's late several time zones away and I appreciate you being flexible in the timing. So thanks so much for taking the time. Everybody listening or watching? We will link to everything we discussed in the show Notes as usual at Tim Blog Podcast. And until next time, as always, be just a bit kinder than is necessary to others and also to yourself. Thanks for tuning in.

[Tim Ferriss (Sponsor/Ad Reads)]

Hey guys, this is Tim again. Just one more thing before you take off and that is five Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun before the weekend? Between 1 and a half and 2 million people subscribe to my free newsletter, my super short newsletter called 5 Bold Friday. Easy to sign up, easy to cancel. It is basically a half page that I send out every Friday to share the coolest things I found or discovered or have started exploring over that week. It's kind of like my diary of cool things. It often includes articles I'm reading, books I'm reading, albums perhaps gadgets, gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcasts, guests. And these strange, esoteric things end up in my field. And then I test them and then I share them with you. So if that sounds fun, again, it's very short. A little tiny bite of goodness before you head off for the weekend. Something to think about. If you'd like to try it out, just go to Tim Blog Friday, type that into your browser Tim Blog Friday. Drop in your email and you'll get the very next one. Thanks Watching for Thanks for listening.

[Tim Ferriss]

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[Tim Ferriss]

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[Brian Dean]

This is what it does.

[Tim Ferriss]

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[Tim Ferriss (Sponsor/Ad Reads)]

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