Landon Ray – Founder and CEO of ONTRAPORT

Communicate way more than you think you have to — with clients, with your teammates, with your partners (in life and business), and with any other stakeholders. It’s incredible how challenging communication is, and what havoc miscommunication creates.

Landon Ray is a serial entrepreneur whose mission is to educate, motivate, and enable others to realize their life goals and passions by starting and growing their own businesses. At the age of 25, Ray transformed himself from a street corner flower vendor into one of the nation’s top securities day traders in only 12 months; his success was recounted in books, magazines, and dozens of newspaper articles across the country. Today, Ray is the founder and CEO of ONTRAPORT, a 6-year-old company that has thrived during one of the worst economic downturns in U.S. history. After beating the odds on Wall Street and again during the recession, Ray has taken his exhaustive research and personal experience and created a family of products and related services that reflect his passion for educating and supporting entrepreneurs. ONTRAPORT is an award-winning all-in-one marketing and business automation platform designed to help entrepreneurs start, systemize, and scale their businesses.

What are you working on right now?

I’m working on a lot of things. My primary responsibilities are product management (figuring out which features/products we should build, designing them, writing the specs, and working with graphic designers and engineers to get them done) and general direction-setting for the company as a whole. Also, I write a lot: blog posts, talks, etc.

Where did the idea for ONTRAPORT come from?

ONTRAPORT came out of our own needs. I was running another business and ran into the problems that all entrepreneurs do, and I couldn’t believe there wasn’t a slick solution to solve them. We started building them for ourselves, and then realized we were on to something pretty cool. We decided to release our internal toolset as a product. That was a long time ago (eight years!), and ONTRAPORT has been through a ton of changes since then, including two complete rewrites.

What does your typical day look like?

We have a unique work schedule here. Everyone in our company shares two 90-minute periods each day where we have “time block.” “Time block” is the time during the day when everyone works on their projects (not their normal business maintenance), and we have total communication silence — no chats, phones, email, or walking over and bugging anyway. It’s focused time to move the business forward. You can read more about that here: .

How do you bring ideas to life?

I think the key is to spend quiet, focused time really getting clear about your goals, looking at things from many perspectives, being as strategic as possible, and then checking in with people you respect to get feedback. Once an idea is crystal clear, it’s a lot easier to have the end product look like your vision. As for getting things done, I’m insanely lucky to have an amazing team of more than 50 people who are expert, committed life-bringers for ideas.

What’s one trend that really excites you?

I’m obviously pretty excited about entrepreneurship and the massive increase in the number of people who are taking the plunge into starting their own businesses. I think the confluence of wider availability of great education, much better technology tools, and a ton of smart, experienced Baby Boomers retiring from their careers — but not yet ready to call it a day — are all major factors contributing to the enormous energy around entrepreneurship right now. It’s really exciting stuff!

What was the worst job you ever had and what did you learn from it?

I worked for a painting contractor, mostly taping windows, doors, and light fixtures before the spray guys would come through to paint, and then cleaning up after them. The bummer was that this guy’s success equaled the difference between what he could collect from the homeowner and what he had to pay us, so in his eyes, we were the problem. Pretty much every day, all day, he was literally standing behind us, yelling about what idiots we were and to hurry up.

The lessons were many. Don’t work for a jerk. Don’t do a job where you are seen as a “cost,” instead of a provider of value. Also, don’t ever create a business where your people are seen that way because as much as life sucked for me in that role, I’m sure it sucked for him even more.

Obviously, I didn’t stay long. And I’m sure no one with any brains did, either.

If you were to start again, what would you do differently?

I’d like to think that I could do it differently if I could start over, but more than likely, it would look pretty similar a second time around. It was a lot of failure and learning things the hard way.

If asked to give advice to a new entrepreneur, I’d say to focus first on making absolutely certain that there’s a market for what you want to sell and to invest as little as possible before that. Steve Blank’s book, “The Four Steps to the Epiphany,” explains the methodology for getting this right.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Communicate way more than you think you have to — with clients, with your teammates, with your partners (in life and business), and with any other stakeholders. It’s incredible how challenging communication is, and what havoc miscommunication creates.

What is one business idea that you’re willing to give away to our readers?

Doing work in your business is not building a business. Building a business is about building systems to do the work. If you’re not building systems, you’re building a job, and a home-built job is never going to get you what you set out to get when you decided to become an entrepreneur.

Tell us a secret.

I’ll keep mine. Here are a bunch of other people’s secrets: .

What are your three favorite online tools and what do you love about them?

● Google Apps: It has great tools, all in one piece of awesomeness.
● Jing: It enables you to capture easy screenshots and short videos.
● Smartsheet: This produces killer spreadsheets that we use for project management.

What is the one book that you recommend our community should read and why?

Seth Godin’s “Purple Cow” and “Raving Fans” by Ken Blanchard are both must-reads. Both of these books really do a great job of giving you new perspectives on creating extraordinary experiences for clients, and I credit the ideas I got from them with a lot of our success.

What’s on your playlist?

I listen to Built to Spill, Jeff Mangum, Jeff Buckley, Prince, Wilco, and John Frusciante.

If you weren’t working at ONTRAPORT, what would you be doing?

I’d be reading and writing a lot more, probably somewhere tropical. I’d probably be helping other entrepreneurs think through strategy as an advisor and/or investor.

Three people we should follow on Twitter and why?

I don’t know anything about Twitter. Sorry. It looks like a giant time waster to me. I mean, does anyone really look at their feed? Once you follow a few dozen people, it’s freaking ridiculous. It’s all static, it seems to me. The only time I look at Twitter is when I use the search feature when there’s a breaking news story.

When was the last time you laughed out loud? What caused it?

I probably laughed at something on Reddit. Last night, I watched “This is 40,” which is an absolutely horrible, painful-to-watch movie that I don’t recommend. But I probably laughed.

Who is your hero?

I don’t go in for heroes much because I recognize that we’re all pretty much human, doing our best. But if I had to name a few people I really respect, I’d go with Richard Branson as my entrepreneur/business hero and Werner Erhard as a personal hero. Both are amazing, inspiring people and powerful leaders.


Landon on LinkedIn:
Landon on Twitter: @LandonRay
Landon on Google+: