Behind-The-Scenes: How I Built Live Your Legend from Idea to Profitable Online Business

LYLL Budapest and me over excited

Behind-The-Scenes: How I Built Live Your Legend from Idea to Profitable Online Business

“The interesting thing about entrepreneurship is that it never seems to end.” – Unknown

Time Sensitive: Live Your Legend RAW is open to new members for the next 5 days (until Tuesday 4/21 at 11:59pm PST).

We created LYL RAW as a resource for those of you building your idea, passions, talents or expertise into a business or side-income. It’s my way of giving you a window into my head – uncut, behind-the-scenes access to how I’ve built the LYL business and community, plus weekly guidance and lessons to support you in building your own profitable passion project. It’s a level of business detail I don’t cover publicly on LYL.

I’m in love with the way it’s turned out and how it’s helping the builders and makers in our community like we never have in the past.

Check it out and try it risk-free here.

Now, let’s chat a bit more about building businesses…

From Nothing to Something Tangible

Above is a picture of Live Your Legend Local’s Amsterdam crew, taken last Sunday after a few intense (and awesome) hours together. We had expected 15 and about 50 showed up. I think the ongoing (and unprompted) yelling and screaming about got us kicked out of our family brunch joint venue, which made me pretty proud.

We’ll be doing the same with the LYLL crew in Budapest tonight, after I explore one of these Hungarian bath houses everyone’s telling me about.

Spending time with so many of you, in person, hearing your big ideas, plans, fears and struggles, puts things into perspective like no piece of technology or social media ever could.

It also reminds me how many of you are building amazing things, and how incredibly often I get the question…

“So how does Live Your Legend make money?”

I get versions of this all the time.

And often it starts out in a tone that comes across more like,

“So… does Live Your Legend make money??”

I literally get this at every event I go to (as well as from a surprising number for acquaintances and extended family). And it always makes me laugh. I mean, what do people think? I work my face off on this business and movement, I have no other job and my wife and I are on a yearlong trip around the world. Plus, how else could I invest so much time and money into our product-level free resources like this blog and our LYL Local communities?

But while I can’t expect everyone to know the ins and outs of how LYL makes money, I want you all to, with the hopes that it helps you make the progress you want to make.  

Because, while at times this question comes from skeptics, I mainly hear it from so many of you who’ve been around LYL a while and have your passion and/or idea nailed down enough to start taking a crack at turning it into a source of income – either as a side-hustle or full-time gig.

I love helping people through this phase, and haven’t gotten to do it often enough, so today I’d like to share a little bit about how it happened to me.

How we went from no one knowing the words “Live Your Legend” a few years back to hundreds of groups of people, many in cities I’d never heard of, hosting their own monthly LYL Local events.

And how LYL somehow went from zero dollars in revenue to making more per month than my entire annual starting salary at that first miserable Fortune 500 job of mine – the one that forced me to quit and eventually start LYL. How’s that for irony??

So let’s dive in…

Building Live Your Legend into the full-time business it is today went something like this…

About a decade ago I was in serious pain (hated my job). I quite, started experimenting, and did everything I could to figure out how to solve my problem. Most things didn’t work, but some did.

As I found what worked, a lot of friends asked for my help with the same pain. So I helped. And in helping, I learned better ways to help.

I then started to write about my ideas (what was working and what wasn’t) and posted them online as an experiment. It was a blog before I knew what a blog was. At first I was terrified to hit publish (sometimes I still am).

I expected a lot of people to start reading, but almost no one paid attention – for the next four years.

My wife couldn’t understand how I could spend so much time on something and still not see any tangible (or financial) results from it.

I was frustrated and thought about giving up. 

But the experiments continued.

I started to learn about online business and community building. I joined some forums and courses and started to meet people who had done what I wanted to do. Some of it was useful. A lot of it wasn’t.

But some of those people and ideas inspired me, so I spent more time around them. Some of them became friends, models and mentors. They showed me what worked, what didn’t and what was possible.

I could finally see a path, and that got me incredibly inspired.

I started to get more specific with the challenges I helped people solve, and started to write for a lot of other sites.

More people started to pay attention and join the community.

One day, I fearfully offered a paid service to work with people one-on-one (after my coach all but forced me to “start charging people”). To my surprise, people started to sign up and I made my first dollar. Then my first thousands. I could feel the potential.

Working 1:1 got me intimately more familiar with their challenges, and I noticed many were the same.

I continued to offer as much free value to the community as possible and it continued to grow. There were a lot more people who needed help than I could provide through hourly work. I needed something more scalable.

After a lot of (healthy) pressure from a mentor and friend, I decided to create my first course, Live Off Your Passion.

I sat paralyzed in fear for a few months before I actually started making progress. I was terrified, I had writer’s block, I procrastinated, I didn’t have a clue what I was doing. Come to think of it, that’s not the first time I felt that way.

But I learned how to do the right customer research, create a course, set up the technology, figure out a launch timeline, write a sales page (which was terribly ugly) and release something to the world based on what our community actually asked for and needed.

And people started to buy it – a lot more than expected. 

Revenue for the month was nearly as high as my highest previous annual salary. It’d be easy for an outsider to look and say it took a month to make a year’s salary, but those people weren’t around for the 4+ years leading up to it…

Chelsea, my wife, finally started to understand. So did I. 😉

My expertise started to grow, and I was asked to give a TEDx Talk, which I almost turned down out of fear (despite it being a 10-year dream of mine). That talk ended up having the biggest impact of anything I’ve done.

Corporations started to offer me four and five figures to give an hour-long talk. I turned down the first few because I was “too busy,” but I think that was my way of saying “I’m too stressed and scared and I don’t think I deserved to be there anyway.” Yes, I’ve felt like that once or twice.

Strangely, as the business grew and became more of a certainty (although it never is), the complexity, stress and fear started to grow alongside it.

As I identified more places where the community needed help with something I was talented and passionate to provide, I created more products (most of which I timidly contemplated long before acting upon). They grew the business and helped a lot of people.

I had to pinch myself with what LYL had become…

But all that also managed to make things a lot more complicated.

I hired my first employee. Then another. And a few more. Most have been amazing, but over the years I had to let a couple of them go, and one decided to quit right at LYL’s most crucial growth point to date. For a few days, I wondered how I’d recover.

At one point the pressure (both of leading something that had grown far beyond expectations, and of having to make endless decisions with imperfect information in a world where I still felt like a beginner in so many ways), about put me down.

While I felt like I’d made so much more progress than I ever could have scripted, in some ways I felt like I was going backward. I’ve started to realize this feeling is a cycle that seems to repeat (or at least rhyme), every 6-12 months or so.

But I stayed close with my peers, friends, mentors and mastermind group and I hired a business coach – all of which helped tremendously (as well as my wife and Chief Balance Officer, Chelsea, and a full-blown “stress management campaign,” which I’ll write more about one day).

The stress all but disappeared. Then it came back a little. Then it went away – mostly.

And that’s about how it’s gone.

A lot of highs. A few serious lows. And a business, life and community I’m beyond grateful for (still in awe).

And eventually it all led me to right here… to this tiny crooked table on the balcony of this week’s apartment in Budapest, overlooking a bright yellow church with a bell tower that says hello to my wife and me at the top of each hour. And a few dozen Living Legends down the street, waiting to welcome us to their city (and yes, I still do get a little nervous on the way to each event).

Yup, that’s about how it happened.

Got it?

Wait, what? Did that sound too simple?

Yeah, that’s because it was.

And that’s the problem with taking a crack at things.

Most people tend to make it sound so much damn easier, simpler, cleaner, faster, clearer, fearless and more obvious than it was. And most onlookers like to assume the same.

This lack of transparency is a tremendous disservice to those of you trying to build your own thing.

It screws up expectations, which leads to frustration, which makes you want to give up. And that is the last thing I want for all of you.

Because there is A LOT that happened between the lines in that story up there. It would be impossible to cover it all in one post (this article is already long enough!). And most of it is outside the scope of what we usually cover on LYL.

And that’s exactly why we created Live Your Legend RAW.

Consider LYL RAW your front row seat to a personal, behind-the-scenes “Open Mic” session with me, answering your biggest questions & challenges and sharing the ins and outs of how I’ve built Live Your Legend into the profitable and sustainable business it is today, with weekly lessons and actions to help ensure you build your own profitable business from your talents, passions and expertise.

Because, here’s the thing…

It. Never. Ends. 

I’ll always be building, experimenting, screwing up, learning, improving and growing.

And I hope nothing but the same for you.

We’re in this together – and I want to be in your corner the whole way.

Finding and doing work you love never ends.

And that is the best part.

Next stop for us is an overnight train to Transylvania this weekend. Let me know if you’re in town.


– Scott

Click here to learn more about Live Your Legend RAW.

It comes with a risk-free guarantee and costs less than lunch with a friend. If it’s for you, I hope you’ll at least give it a try.

Your last chance to join is this Tuesday, April 21st at 11:59pm PST.

Join Live Your Legend RAW here.