The Hideous Start to Live Your Legend: 8 Years of Screen Shots & Steps Revealing How I Built My Business

The Vision for LYL before anything existed circa 2009

The Hideous Start to Live Your Legend: 8 Years of Screen Shots & Steps Revealing How I Built My Business

“A path begins by walking. The best place to start is at the beginning. And usually it ain’t that pretty – especially at first.”

The Purpose of the Post: Many of the screenshots in this post make me cringe. They show every step I’ve taken from first website to Live Your Legend today. And each step has in-depth explanations of my psychology and strategy (or lack thereof) at the time, including many links to deeper resources. All numbers mentioned are estimates since I didn’t keep exact track at the time.
It’s in-depth on purpose and meant for those of you fighting the good fight in building what matters – to give you an honest, real-world look at things. And for the rest of you, at least you’ll have something to laugh at…

But First Some Time-Sensitive Fun:

In honor of today’s post, the recent rebirth of the new Live Your Legend site and the tremendous respect I have for one of my biggest mentors turned close friend, Corbett Barr, we’re doing something special just for you.

Corbett coded, designed and launched the first LYL three years ago, and two weeks ago, he and his business partner Chase Reeves created the new LYL, which I’m incredibly proud of. It’s proving to be massively successful both in the quality, image, message and brand it communicates, and in the increased conversions and metrics that have come with it. More on that later, though.

For now, know that Corbett has offered something very cool to all you Living Legends: try out Fizzle – his uber-useful online business training & community for 30 days for $1. Yes, $1.00. Without question, it’s the best deal on the Internet, with zero strings attached. Fizzle contains everything Corbett has trained me on over the years and a ton more.

Plus, those of you who join before Sunday, December 21 at midnight PST will get a free coaching session with Corbett and Chase to cover any and all questions you have about how they created the new LYL – and any other online business building questions that come to mind.

You’ll also get a free copy of my Live Off Your Passion Lite course.

There are very few things I can stand behind 110%, especially when it comes to online business building. Fizzle gets my approval without reservation.

Click here to check out their crazy video and join Fizzle.

Now, for some fun and a little taste of the magic Corbett has sprinkled on our revolution over the years…

Today, we’re taking an embarrassing walk down memory lane…


Because no one ever likes to pay attention to where things start – and it’s a tremendous disservice to anyone trying to build a life they’re proud of and make their own difference in the world!

Human nature seems to lead us to assume things are easier for others than they are for us. Or worse, we assume that people who are doing well did it without much effort, so we expect the same for ourselves.

And that’s exactly the type of expectation that causes people to give up after the first month or two. 

That is the last thing I want for you.

So in the never-ending Live Your Legend thread of authenticity, we’re going to pull a few skeletons out of the closet.

Today’s are in the form of screen shots that literally make me cringe.

I hope you’ll enjoy starting from the beginning with me. The good news is that given the path we’ve laid out at LYL using incredibly high-quality tools (like Corbett’s Fizzle), you do not have to fumble around in the dark nearly as long as I did.

Now, enjoy the show…

Circa June 2006 – Scott Dinsmore First Hits the Online Scene

I had just left a Fortune 500 job in San Francisco that was causing me to daydream about banging my head into the keyboard.

The day I left, my friends sent me a “retirement” balloon. It was incredibly embarrassing – especially when I asked my boss to take a picture that I miraculously found on my hard drive last week…

My first retirement balloon

The only saving grace of my corporate gig was my 90-minute round-trip train commute where I picked up a reading habit.

When I quit (after 7 loooong months), I went to the bookstore like usual and grabbed 10 books that looked interesting. I then sat down to read the first few pages of each to make my choice. One claimed you could start a website without knowing code, which seemed like the perfect challenge at the time, so despite its slightly suspect name (Internet Riches by Scott Fox – a guy who’s since become a friend), I took it on.

I created an account with Yahoo Site Builder and within a few weeks, I was live with the masterpiece you see below: Reading For Your Success, where I wrote book reviews and recommendations on everything I was reading. Apparently it was a blog for about four years before I first heard the term.

And I was incredibly proud.

Notice the fine use of colors, spacing and advertising…

My First Website Reading For Your Success

Oh, and as luck would have it, I just did a search for “Internet Riches” on LYL and came up with my original unedited book review. Have fun with this one.

My masterpiece even had links on the left that you could click (and I even coded what color they turned!)…

My First Gorgeous Website Reading For Your Success v1

Guess who designed that baby… from scratch?


Guess who dreamed up the logo (and designed it in Microsoft Word)?

That’s right.

And in case you were wondering – the little yellow bush in between the R and the S represents the “yellow wood” in Robert Frost’s poem, The Road Not Taken. And yes, the bush also doubles as an F and a Y.

In fact, the poem is still live on LYL (I just searched and found it!) – here’s the unedited version from 2008 or so. I should probably clean that one up.

Okay, so this is right about when I thought the advertising revenue would start rolling in.

I didn’t expect any subscribers because:

1. I didn’t know what that meant.

2. Even if I did, there was no way for people to do it.

In case you’re wondering a little more about the Why of RFYS, you might enjoy the prose on my About page…

About Reading For Your Success

Circa 2008 – Scott Meets WordPress

So for the first two years I wrote reviews, tweaked my site (endlessly and senselessly) and my audience proceeded to grow by exactly zero. Other than my loyal followers (mom, dad and Chelsea), this site got just about zero traffic with zero growth.

Average daily unique visitors: 7

But I was in love with writing these reviews. After each one, I’d email it to someone specific whom I thought would find it useful.

So far, so good.

Then my friend Pat, who subleased office space from BioIQ (the preventive healthcare startup I worked with for two years after my corporate disaster – a company, culture and team that I was in love with and am still close with the leadership team to this day), told me about this cool thing called WordPress. He said it magically allowed you to edit the page without knowing code and make it really easy to write, post and update things. And was good for SEO (whatever that was).

This was also about the time I read Tim Ferriss’s 4-Hour Workweek, which had me obsessed with outsourcing (among many other things).

So I hired a team in India via Elance, for like $8 an hour, to convert my baby to WordPress.

That brought us here…

So proud.

Reading For Your Suceess v2

Now I was really in love.

And yes, I was still the lead logo and site designer. But now I had a way for people to subscribe!

For the next two years (four years since RFYS first went live), I got about exactly 112 subscribers and continued to get nearly zero traffic growth. I’m pretty sure every one of those 112 were people I knew in the real world who were just being nice.

Average daily traffic: 14

I was still in love with the writing, and people were actually starting to come to me for advice. Especially advice on changing their job.

I started to have lunch with them and share the ideas I’d discovered in my reading and experiments.

Not long after that, my quit rate hit around 80%, which meant that of the people I met for lunch, 80% would quit their job in the next 2-3 months to pursue something more meaningful.

While I’ve since realized that “just quitting” is rarely the right short-term decision, I was damn proud of my 80% stat at the time.

I didn’t necessarily offer much unique magic in these meetings, but I did ask a simple question that seemed to really rattle people…

Why are you doing what you’re doing?

As soon as they uttered the words, “Um… because I’m supposed to…??” out loud, as almost everyone did, they got the feeling something probably needed to change.

Circa 2010 – I start to learn something useful (about the web)

From day one, building RFYS was priceless as it quickly became my petri dish for my experiments, personal branding and writing. It was my first experience getting to leverage The Three C’s For Cultivating & Pursuing The Spark: Consumer, Create, Connect.

This is why I am constantly recommending that you all create a blog. Not because you should build a business around it (some of you might later decide that, but that’s not the point). I recommend it because it’s the most productive and inexpensive tool I’ve seen for building your personal brand and developing, testing and sharing your passions, talents and strengths with the world.

That’s why I created the free 7-day Start-A-Blog Challenge – to teach you all how to build a successful writing habit and leverage it to find your dream job (even with zero tech experience).

Very Important Note: If I were measuring by outward metrics at any point in these past four years, I would have been incredibly disenchanted, frustrated and probably would have given up. But I was measuring by something different – the stuff that was in my control and that I actually cared about. That was reading books, writing reviews and sharing them with others. Warren Buffet’s concept of having your own Internal “Yardstick” is crucial when building (or doing) anything meaningful. Measure by what everyone else tells you you should care about, and you’ll most surely give up too early.

So, this is when I actually started to learn what was involved in building a blog (and when I learned what I had was a blog)…

By the way, this was right after I had started to get really frustrated and defeated after four years of zero external growth. Following that yardstick is often easier said than done.

But that’s right when two important things happened:

1. A long-time mentor, entrepreneur and investor friend of mine gave me the book Inbound Marketing by Brian Halligan and Dharmesh Shah (yup, that’s another link to my original unedited book review).

This book was brilliant in its simplicity with checklists at the end of every chapter. I remember reading it on the flight home in January of 2010 and had this realization that I had the perfect petri dish for checking off the tasks at the end of the chapters. And I LOVE lists.

2. I moved to San Francisco and, for the first time, started meeting people, both online and in person, who had these incredible online businesses that leveraged their talents, strengths and passions to not only help people in a meaningful way, but also to provide an incredible lifestyle for their families at the same time. My mind was blown!

Being inundated with these people became my Roger Bannister moment.

And my now good friends Leo Babauta and Corbett Barr were the ones crushing the metaphorical 4-minute mile.

The two started out as the kind of people I saw as untouchables. You know, the guys who make you feel starstruck. But over the past few years, that’s changed a bit. Last year Leo and I ran a 50-mile ultra-marathon together, tonight Corbett and our ladies are going on a double date to the Warriors game, and last weekend all three of us (and our wives) were up until 3am on Friday and Saturday nights at both of our holiday parties.

It’s amazing to call both those guys such good friends.

So, one of the first things I learned was that I needed a reason for people to subscribe (opt-in) to my email list.

So I published my first eBook and had the cover designed for $5 by someone on Fiverr

Reading For Your Success free ebook!

Circa mid 2010 – I hire someone for the first ‘big’ redesign

My first real financial investment into LYL came when I decided to hire a designer to do a bigger overhaul to create a new header and logo (shed a tear) and move my site to the Thesis WordPress theme (which seemed to be the most popular at the time).

I paid a grand total of $500, I believe.

And that was big money.

I was so damn proud of what they created…

Reading For Your Success BIG Redesign v3

Average daily traffic: 195

By now I had learned the incredible power of guest posting and had around 300 subscribers.

My dream was to break 1,000 – at which point I thought all my problems would be solved.

Then it happened. I got a guest post accepted on Zen Habits (which had millions of readers, even back then), long before I actually met and became friends with Leo. I told the story of how I summited Mt. Shasta in California (which happened to be for my bachelor party). Of course, I took a screenshot of it, as I do with all things I’m proud of (a daily/weekly practice that I HIGHLY recommend – I got lost in reviewing years of screenshots as I wrote this post this week)…

My first post on ZenHabits!

This went live on Tuesday, August 24th, 2010 – three days after I married Chelsea. Which meant I was on our honeymoon in Croatia. Which also meant I wasn’t checking any stats. It took all of my restraint to wait until I got home two weeks later.

When I looked, I’d added nearly 1,200 subscribers. My jaw hit the keyboard.

Let this be a lesson: I’ve found no more powerful place on the Internet to grow your audience than guest posts on single-author blogs with very big and loyal followings. I’ve had all kinds of things published on Forbes, Fast Company and Inc. Magazine over the years, and while they are great for brand association and credibility, none of them made a noticeable difference in new subscribers. That’s not to say they can’t, I just know from experience that nothing beats big, focused blogs run by one respectable author.  

This made me really start to see what was possible. I finally had a critical mass of people paying attention – a priceless group of people to further test, refine and grow my ideas.

But, despite me thinking that all my problems would be solved at 1k subscribers, not a thing changed financially (i.e. my income from RFYS was still precisely zero).

Circa July, 2011 – I get serious, hire Corbett and launch Live Your Legend

By now, I was convinced at the potential of my vision for what I planned to build. It was by no means certain. But I felt incredibly certain that if I put my head down and gave massive attention to executing on the path I’d been taught by people like Leo and Corbett – and did everything I could to change the lives of my readers – something powerful could be built.

My four years of spinning my tires with RFYS also taught me something priceless…

While I wanted to write about every personal development topic under the sun, where I knew I could add massive value was helping people make the change to doing work they actually cared about. That’s the “metric” that’s impossible to measure in Google Analytics, but was a very, very real growth area during my four years of zero tangible growth.

This is right about when Leo, while we stretched after a long run, compassionately said something along the lines of, “Scott, if you want to build what you talk about building, I think you need to change your brand.”

It was tough to hear, but I knew he was right.

If I were thinking up a brand from scratch that day, the term Reading For Your Success would have had nothing to do with it.

And that’s a crucial point. For weeks, I was trying to see how RFYS fit into the new brand. But I was only doing that because I was psychologically committed and invested in what I’d spent four years building, not because there was any rational sense to keep the old brand. Commitment Consistency is a powerful thing, though – you’ve been warned. 

That’s also about when I hired Corbett, who’d already taught me a ton about the nuts-and-bolts tactics and strategies of growing an online business.

As obvious as this seems looking back, it was an incredibly hard decision. He was pretty much retired from building and designing websites for people, which meant he had no interest in lowering his $4,000 rate (and he shouldn’t have!).

That money may end up being the best investment I’ve ever made for my career.

The amazing thing about Corbett’s background is that he’s not just an unbelievably talented coder and engineer. He also knows design. He knows user experience. He knows branding. He knows the dynamics of a successful launch (all of which is is covered in Fizzle’s video training modules). And he’s run venture-backed startups. So he’s able to see the whole picture in a way that most people never could.

And that’s probably why, when we finally launched Live Your Legend to replace RFYS, our email subscribers literally doubled in the first week.

That wasn’t even part of my plan.

But something about the combination of the refined and focused brand, our launch strategy and a bunch of hustle caused the LYL subscribers to grown from 3,500 to over 7,000 in just over seven days.

Here’s what “we” created – a screenshot I pulled from the Way Back Machine this morning, taken on Oct 18, 2011. For some reason, it wouldn’t load the page from the July launch.

I was so damn proud…

The Launch of Live Your Legend

And this was our home for three years straight.

This brand and design took LYL from…

  • 895 uniques a day to 5,000 (7,240 on launch day vs. the prior average of about 325)
  • 3,500 subscribers to nearly 70,000
  • Almost no revenue to multiple six figures

Sure, we made some tweaks along the way. Most of those caused the site to eventually look like Frankenstein (thanks to me hacking together most the changes).

November 30th, 2012 – My TEDx Talk goes live and I finally create a feature box

Things changed in a crazy way when my TEDx Talk went live. This was definitely the biggest inflection point of my career. You can read more about it here, here and here.

And going live also lit a fire under my ass to do a few things that had been on my list for months – or years. The biggest one my mentors had pounded into my head was to create a Feature Box on the homepage. This is a place above the fold (i.e. you can see it at top of page without scrolling down) that clearly tells people what benefit you offer to them and asking them to take a specific action (i.e. subscribe).

I cannot believe I wanted nearly a year to actually implement this. It lead to well over a 100% increase in my conversion rate, right at a time when the site was getting a ton more relevant traffic from my TEDx YouTube.

For the details on what I changed and why, read and watch this: 5 Overnight Changes that Grew Our Community & Conversions by 2-3x: Derek Halpern Dissects LiveYourLegend

The LYL Feature Box 25k subscribers

This is right about when we hit 25,000 subscribers.

Average daily uniques: 3,500

A LOT obviously happened between this time and today, but the site really didn’t change much.

In looking through my “screenshots of pride and gratitude,” I came across this Instagram picture created by Monet Diamante, one of our incredible Connect With Anyone graduates, who’s since become a real-life friend. She posted this around September of 2013. I think it sums up the state of LYL just about right. Love this woman!

The photo was taken of my dad (AKA LYL Chief Strategist) and me in Hawaii in 2013. Monet added the text…

The LYL Community and my dad

We had about 41,000 subscribers when that picture was taken.

Friday, November 14, 2014 – The totally redesigned and repositioned Live Your Legend goes live!

This is the moment I’d waited for for nearly two years.

After the TEDx got so much traction, I realized that the current LYL brand did not represent the quality and positioning that it had grown into.

But one of the huge challenges was finding the right designers.

Because, as far as I’m concerned, redesigning a site is NOT about the design. The quality of the design is a result, but it is not the point.

The point of redesign is communicating a brand (through colors, images and copy/text) that resonates with the people you’re trying to help and how you’re trying to help them. The copy or words on the page are incredibly important. So is the flow of the site, the lack of clutter and the usability. All of this comes together to cause people to (hopefully) make the split-second decision to stick around instead of leave, and ideally subscribe to your email list.

The huge problem is that most designers do not get this. Not even close. Nor should you expect them to. They’re artists. And that’s awesome. But to expect them to know how to incorporate messaging, branding, design, user experience and conversion optimization is ridiculous.

And that is why there was only one person (well, two) I was interested in working with for the new design – Corbett Barr and his design genius partner Chase Reeves at Fizzle.

They not only know the whole world of online business, start to finish, but they also know me intimately as a person and the Why behind what I’m building at Live Your Legend.

This is also why it took about 1.5 years from the day I decided it needed to happen, to actually going live with the new site – because unfortunately, Chase and Corbett do not do design projects for clients. That’s not their business. They are more than busy building Fizzle – their super useful online video training library and community for building an honest online business.

The only sites they’d done in the past were Think Traffic (Corbett’s old site), Pat Flynn’s Smart Passive Income and Steve Kamb’s Nerd Fitness. And they didn’t do those for the money – they did them because Pat and Steve are close friends and they wanted to help take their movements to the next level – and indeed nailed it.

So I waited about a year to start the project, until Corbett and Chase were able to free up some time.

And I’m glad I waited, because I learned a ton more about our brand and community in that year.

Specifically, I discovered that the foundation of what we do is community – we help you find and do work you love by surrounding yourself with the people who make it possible.

That’s become LYL’s secret sauce. Which led to our Connect With Anyone course and our free Live Your Legend Local meetup groups around the world.

So the timing ended up being perfect.

And despite the seemingly large price tag for the new site (gotta keep that one private for now), I was 100% certain it was the right thing to do.

And this was massively reaffirmed when Chase and Corbett insisted that the first step of the redesign was me committing to having 10-20 30-minute 1:1 Skype calls with my most dedicated users (another thing most designers would never insist on).

This was priceless, not only for the new design, but also for the future of Live Your Legend. Those interviews told me to create the Make Your First $1,000 Workshop, build a new platform for LYL Local (launching in a few days!) and create a totally new product that I cannot wait to announce in early January 2015.


You do NOT know what’s in their head. You do not know their pain. THEY do.

This launched us into about a six-month process from start to finish and has given me the most pride of anything I’ve ever attached my name to…

For contrast, here’s what LYL looked like the day before the new site went live (homepage):

Live Your Legend right before new design homepage

Here’s what the very first version of Reading For Your Success looked like (in 2006):

My First Website Reading For Your Success

And here’s the masterpiece that Chase, Corbett and my other incredible designer/developer Glen brought to life two weeks ago (homepage):

And a blog post page from the old site:

Live Your Legend right before new design blog post

And the same blog post on the new site:

The new live your legend blog post page

Average daily uniques: 5,100

Notice anything different between the two sites??

For all the details of what we changed and why, read my launch post – it explains everything.

What’s incredible to me are the things you probably don’t notice.

Or that you don’t realize you notice. Chase is a true artist and his attention to detail is insane. Ten of the changes he suggested after we went live were things I couldn’t even notice when he showed me where they were.

I mean, the first step we discussed when we actually sat down in Tahoe to work on the design was… the font.

I thought he was crazy. But he explained that the size and spacing of the font, letters, words and lines dictates the dimension and symmetry of everything else on the site. That’s why you could use the same fonts as your favorite site, but for some reason it still just doesn’t look the same.

Another check mark in the column of why I’m grateful to have had the right team on the job.

I could write another ten thousand words about how and why they did all they did, but that would be a waste of your time and mine.

Especially since Chase created a 6-hour video course in Fizzle on exactly how to apply his design methodology to your own site.

You can take Chase’s whole design course as part of their $1 30-day trial period

So, there you have it!

This is the life of the Live Your Legend revolution all the way back to long before LYL was even an idea.

So what’s the point of all this? Why did I just write 4,200 words to show you a bunch of crap website designs??

Because it’s important that you see where things started.

I started with no idea of what I was doing or where I was going.

I started simply to experiment and follow the spark.

I made no outward or visibly obvious progress for FOUR years.

Those years of “zero growth” experiments taught me all the things I needed to know to develop the skills, reputation, confidence, business and movement I didn’t even know would exist at the time.

And to show you that most projects start out looking really, really, really shitty!

But did you notice something about every screenshot?

I was incredibly proud of every one of them – at the time.

Looking back, it’s embarrassing. But that’s the exciting part.

The learning and experiments are cumulative. They compound over time in an even more magnificent way than money properly invested.

And even better yet? Your first site will not look anywhere close to as terrible as mine. Today’s tools make it possible to look gorgeous right out of the gate. And that’s freakin’ awesome.

But the real point is that you have to START. 

So, let’s revisit the goals I sketched out in my Moleskine about six years ago (WAY before I had any idea I’d build LYL)

The Vision for LYL before anything existed circa 2009

When I got serious about Live Your Legend in 2011, I thought I was way too late to start a blog about doing work you love.

But thanks to encouragement from friends and mentors and being certain about my Why (that getting people to do work you love will eventually start to change the world), I charged forward.

And it’s easy to think the same thing today – that you’re too late. And many people will talk themselves out of starting for that very reason.

My goal is for you not to be one of them.

Because those who start today will be the ones who have a shot at changing the world tomorrow. I mean that quite literally.

And wanna know another cool thing? Take a look at that goals sketch. In Year One, I wanted 500 subscribers. That took more like 2 years (from when I wrote those goals and 4 years from when I first started RFYS). Year Two, I wanted 3-5k subscribers. In years 5-10, I wanted to get to 20k subscribers.

My thinking was too small for what was possible, and while it took longer for the early goals, after only 3 years, I hit nearly 5x my 5-10 year goal.

Nothing happens overnight.

But when you get crystal clear on the difference you want to make for others and then get crazy focused on putting one step in front of the other, it doesn’t have to take that long, either.

Four years ago, I’d never said the words Live Your Legend.

Last week, 19 people in Budapest attended their first LYL Local meetup – 17 of whom probably had no idea who I was or maybe even what LYL meant. They came because two of our community members, Laura and Krisztina, decided to spread the movement to their local city…

LYL Local Budapest

This is the kind of stuff that becomes possible once you decide to start.

And despite how ugly and bumpy it is along they way, you decide to keep building, keep learning and keep experimenting.

Thanks for making magic with me, everyone. And for enduring such an ugly slideshow. While I cringe at those first few screenshots, I can’t tell you how fun it was to relive the stages as I created this post. So thanks for that.

I pinch myself everyday,


Oh, and a HUGE thanks to Corbett, for taking an interest in my vision years ago and to he and Chase for finally doing it justice.

Remember, for the next week, Corbett and Chase are offering something very cool to all you Living Legends…

Try out Fizzle – their uber-useful online business training & community for 30 days for $1. Yes, $1.00. Without question, it’s the best deal on the Internet with zero strings attached. Fizzle contains everything Corbett has taught over the years and a ton more.

Plus, those of you who join before Sunday, December 21 at midnight PST, will get a free coaching session with Corbett and Chase to cover any and all questions you have about how they created the new LYL and any other online business building questions that come to mind.

That’s probably worth more than a buck…

And you’ll also get a free copy of my Live Off Your Passion Lite course.

You won’t regret it.

I’m proud to be partnered with these guys in what they’re building.

Click here to try Fizzle out for $1