Brad Feld on the Most Challenging Thing

“The most challenging thing for a young entrepreneur is to think long-term.

When you are 22 years old, it’s hard to think in 22-year increments since that’s as long as you’ve been alive. But it’s really important to view your life as an entrepreneur as a long journey that consists of many short-term cycles. It’s relatively easy to focus on the short-term cycle, such as the 90 days of an accelerator program; it’s a lot harder to think about the next decade and how what you are doing today impacts where you want to be ten years from now.”

Brad Feld

The concept of the long haul has been bouncing around in me for a while. But no one’s made me think about it quite the way Mr. Feld has.

For more from him (and on this concept) check out this interview. This was my introduction to Mr. Feld… I became an instant groupie.

Jerry Colonna on Reality

Face reality.”

Jerry Colonna

What a phenomenal interview. Mr. Colonna can feel a little on the precious side at times but the insights and point of view he brings are gutsy and pungent for me. Remind me of this in a year.

I’ve been listening to this show for about 30 episodes or so. At first I couldn’t stand Calcannis. That’s many peoples’ knee-jerk reaction to him. But he’s growing on me. I think there’s a little more under the surface than I thought.

And I certainly applaud the guy for getting on such great founders and sharing these conversations. I’ve gleaned a ton from them.

Thoughts on Scaffolding, Completed Work & The Creative Process

The first third of every project is building scaffolding. Don’t fear waste. Don’t fear redundancy. Don’t fear inefficiency. Yet.”

Frank Chimero

The balance between scaffolding and the finished product is tricky.

I recently shipped a large project (the scaffolding of which is pictured above). It’s a training course on the essentials of website design for people who who are building their own business. It’s that rare connection of “something I care a great deal about” + “something I know a great deal about.” (There’s a video from the course and more about info about it here).

Throughout the project I moved back and forth between scaffolding (notes on a card or post-it note) and polished words a few times as the structure of the thing emerged over time.

I’d create the bones and say, “yea, that’s good.”

And then I’d write it out and stumble on something that was unclear. I’d work to push through the ambiguity and realize I need to restructure the scaffolding a bit.

This back and forth is a bit harrowing. There’s (more…)

George Lois on Blurbs & Brands

If you have to depend on blurbs to have people buy your magazine then you’ve got a piece of shit! You don’t have a brand!”

George Lois

The same goes for blog post headlines. Note to self: care less about “viral headline lessons.” Care less about short term “conversion” and more about the long term relationship with your audience. Stand for something. Be something. Have conviction. Build a brand.

Jason Santa Maria on the Time Between

…when you’re a kid, everything seems possible. When you think about doing something, the time between thinking about doing it and actually doing it is usually very brief. You say, “Hey, what if I do that?” and then you’re doing it. As an adult, you think, “I want to do this thing,” or, “I want to make something.” Then you start gathering resources and devising a plan, but then you get tired because you’re old and want to lay down. ”

Jason Santa Maria

The Foolscap Method: Get it on One Piece

‘God made a single sheet of foolscap to be exactly the right length to hold the outline of an entire novel.’ (foolscap is 8.5 x 14 inch legal paper)

[…]

Outline the sucker.

Break it down to its fundamentals.

Identify its theme.

Do it on one page. Do it without preciousness. Do it now.

Don’t start the actual writing until you know where you’re going and what you’re trying to accomplish.”

Stephen Pressfield

I think for the first time I just read a thing and knew full well it was going to change the way I worked forever.

This tip has that “ugh, duh! goddamit, of course” quality; like something in me already knew it was true, I just needed someone to articulate it for me.

As I’m in the middle of creating a large and {hopefully) important course for business builders, this tip is about 4 days late.

But I’ll be prepared for next time. (I’ll try that one and go for these if I like it more than using blank printer paper).

One piece of paper… hand written. Duh!

(Vintage) Merlin Mann on Life Hacks

I’ve suffered most of my life from chronic concentration problems and different flavors of mental restlessness, so I have a substantial history of what I call ‘”‘critical encoding errors.’ I’m attracted to this stuff like a drunk preacher is to the pulpit; explaining it to others — inasmuch as my modest skills allow — becomes a way for me to internalize some of the processes as well as better understand why they work in my own head.

As to where I get my material, virtually everything on my site is stolen uncredited from friends and strangers who are too polite to call out my larceny.”

Merlin Mann

This interview is a great reminder of how much Merlin captured my attention at that tender time of my first project management position. He bamboozled me with the mix of wit and jargon and “holy shit that’s useful”-ness. Still does.

Listen to the podcast, get the Matterful Monthly and enter to win free gear.