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“One profession taught me how to understand, synthesize, and simplify, and the other taught me how to break huge, multi-layered campaigns and objectives into doable, easy to communicate, and trackable pieces.”

MO.com is proud to partner with The Young Entrepreneur Council (YEC):

YECThe Young Entrepreneur Council (YEC) is an invite-only nonprofit organization comprised of the country’s most promising young entrepreneurs. The Y.E.C promotes entrepreneurship as a solution to youth unemployment and underemployment and provides its members with access to tools, mentorship, and resources that support each stage of a business’s development and growth.


Charlie Gilkey, the principal of Productive Flourishing believes in helping creative change-makers and entrepreneurs thrive in life in business. Productive Flourishing helps creatives convert those great ideas and intentions into effective action.

They host a micro-business incubator called Lift Off Retreat where in three days they guide participants through the business-building process. Participants walk away grounded in their vision for their business, its strategy and an effective, doable plan of action.

Charlie Gilkey, Productive Flourishing - Principal


MO: Tell us what in your background led you to Productive Flourishing and Lift Off Retreat?

Charlie: First, I’d like to take a second and say thanks for spotlighting what we’re up to at Productive Flourishing and the Lift Off Retreat.

Before I started Productive Flourishing, I was an academically trained philosopher and an Army logistics officer. One profession taught me how to understand, synthesize, and simplify, and the other taught me how to break huge, multi-layered campaigns and objectives into doable, easy to communicate, and trackable pieces. It turns out that those two professions were a near perfect setup for what I do now.

The Lift Off Retreat is a collaboration with Pam Slim from Escape from Cubicle Nation. That came about because, though we loved the people that showed up at events like SouthbySouthwest, we found that the energy was too intense and that the promise of learning great ideas was a bit thwarted due to the intensity.

We had independently mused creating an even where we could have a business retreat that got creative entrepreneurs in person and out of the busyness of their businesses and lives, and the Lift Off Retreat was born.

MO: Can you tell us more about Lift Off Retreat? What kind of activities do your participants partake in? Who are your participants?

Charlie: The Lift Off Retreat is for creative entrepreneurs who are needing some help getting more of a business under their business. They’re usually solopreneurs, but we have had some people with some employees and staffs come, as well. There are two different and complimentary pathway that most people are on:

1) they’re wanting to start a new business and don’t want to spend year flailing on their own or

2) they have a current business that they’re wanting to revision or uplevel. The people in the first track energize the people in the second, and the people in the second serve as great mentors and advisors for the first track.

Participants walk through the process of building their business from the ground up in three and a half days in either Portland or Phoenix – we do two a year in locations close to our respective homes. We move from design, to plan, to action. They map out their offer funnel, do a special type of network diagram that we’ve developed, redesign their offices and workspaces, and actually get down to the nitty gritty for planning all of this out. There are many, more activities, but that gives a pretty good flavor of what happens.

What really makes Lift Off work, though, is the community of people that we pull into the event. Pam and I are blessed to have the most amazing people come as participants and part of the event is the year-long followup we do post-event. The community has currently reached a sweet spot in mass wherein it’s still tight enough for people to feel close to each other but large enough that there’s a lot of diversity, power, and reach within it.

MO: What can we expect from your first book, Beyond Bootstrapping?

Charlie: Beyond Bootstrapping is going to help entrepreneurs and small business owners move from that awkward and terribly uncomfortable stage in which they’re winging everything to the stage in which they’ve got the right people, processes, and systems in place that allow them to grow their business without always increasing their busyness. There are lot of books that get people hooked on the coolness of starting a business and there are plenty of books that help once their business is a certain stage, but there aren’t a whole lot that really get into the trenches of how to get through that period from say the 2nd through the 5th year of business. That’s where so many businesses fail because motivation, passion, and not wanting to have a job aren’t enough to keep your business running and growing.

My creative challenge is making the book such that you can jump in and read any chapter while at the same time making it fit into a cohesive narrative. You might think of it as a mashup of the Effective Executive, The E-Myth Revisited, and Free Agent Nation.

MO: Why did you believe it was time to write the book Beyond Bootstrapping?

Charlie: When we look at the timing for books, you have to look at two things:

1) is the author ready to write this book? and

2) is there an audience or market who’s ready to read this book and needs it. When it comes to the former, I found myself saying the same things about business development over and over again – and my clients, colleagues, and network began gently prodding me to start getting it captured in a book. As far as the market goes, we’re in an unprecedented time wherein the social shifts and technological advancements makes starting a business accessible to so many people. More people are starting businesses – which I see as a good thing – but many are struggling because you have to be smarter, faster, and better in this new world of business.

MO: Beyond the website, you help people through speaking, coaching, and consulting. Personal brand must be very important to you. How have you formed and grown your personal brand?

Charlie: To be honest, the only reason I have a “personal brand” is because I’ve been consistently, prolific, and as close-to-me as possible throughout the years. A personal brand, like a personal identity, is formed through time – I’ve seen too many brands fail because they try to create one out of thin air rather than being who they are.

But branding is more than authenticity, though. The hardest challenge for me has been to give people an easy way to understand who I am – my colleagues and friends have lovingly shared with me that even they find it hard to describe me and what I do. I guess that’s the downside of being a philosopher, a former logistics officer, a business advisor, and a creative polymath, to boot.

The way I’ve handled that challenge is by continually pulling away all of the unnecessary layers and protective shields that so many of us put up so that we don’t stand out. It’s hard to claim the fact that you’re a weirdo or outlier a lot of the time, but in the end, that’s the only way people are going to be able to understand and talk about who you are.

MO: After the books comes out, what will be your next big project?

Charlie: Beyond Bootstrapping is just the first of many books, so I’ll be starting the second one before the first one hits the shelves. Sometime in Q3 or Q4 of 2012, we’ll probably start developing our own web apps – we have too many planners, frameworks, worksheets, and app-able ideas to just leave them laying around.

What I’m really excited about, though, is the communities we’ll be building starting this year and into the future. I can’t reveal too much about this yet, but keep an eye out for how we’re galvanizing the community of creative changemakers.

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