Small businesses have a tendency to grow a little. The founders move out of the garage and into an office. Part-time and then full-time employees start to appear. Business goes well–and then it hits an almost invisible hump. Well before bootstrapping is over, the business is too big for the founders to run on their own. As the giants, the founders hunker down and brace themselves under the heft of the team standing on their shoulders. Somewhere in there, reality strikes. The team has to step forward and the founders have to roll the responsibility onto their shoulders. If the founders hold on too long, they collapse under the weight. If the team steps off early and isn’t ready, the founders watch as their fledgling company crushes their workers. When giants are working with humans, it takes maturity, balance, and vision to keep the company rolling forward.

“It’s tricky for the owners to let go,” Rich says. “You see companies where the owners can’t let go and it crashes and burns.” It takes maturity for a founder to do what is best for the business. Think of it. You’ve lost sleep over this. You’ve sacrificed family time (hopefully not all of it). Whatever it is you’ve done, you’ve poured your heart and soul into your enterprise. If the company grows, you can’t baby it forever–but by the same token, growth isn’t necessarily eternal. Walking that line means making decisions with your head as well as with your heart. You love the feel of that team standing on your shoulders. Each colossal step forward shakes the earth. But giant though you be, you’re still a mortal. Be mature enough to trust your team.

Trusting your team and shouldering the burden is always a delicate balance at first. They didn’t keep a futon in the office for six months. They have a steady income. They haven’t seen everything you have, so shifting the burden starts with little things. “A great example is this monitor,” Rich points out, one that had died a few days earlier. The team member poked his head into Rich’s office and asked what to do. Rich remembers how before, he might have dealt with the problem himself. Now? “What are you going to do about it?” he asked. Obviously the owners keep their eyes on things, but having your eyes on a project is different from being up to your ears in it. Ron adds that “one of the things we’ve also seen is that we’ve got guys . . . who’ve come from more of a corporate background. [Their] initial attitude is, ‘Those guys are the founders. They’ll take care of it.’” Ron shakes his head. “Some of it’s environmental, but some of it’s physiological.” Some team members naturally invest themselves in the survival of the business. Others need to learn. For both, there is only one way.

That way is the vision. Helping your employees catch this vision at the appropriate time keeps things rolling. “So oftentimes people look at the physical compensation,” Rich says. “Typically, that’s the smallest compensation in a company of this nature. What [our team is] using, five-year-college-grads couldn’t get the knowledge.” They need to lose sleep the way the owners lose sleep. They don’t just have to sweat deadlines; they have to sweat bullets. “Give guidance, direction, and incentive,” Ron says. Rewards or profit-sharing programs help take the team from balance to vision. For me, if I stick this out, I have a career path. If I don’t, I putter along and fizzle out. In bootstrapping, make or break is not one day or one deal. Make or break is the whole tenor of the work. Humans have to step down and race forward. Giants have to let work roll onto the team’s shoulders. When that happens, fire doesn’t belong alone to the bellies of the founders. Fire fills the office, the enterprise, and the vision of the future.Estrogen
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True to the company culture at CastleWave, when time came for Rich and Ron to give me the next round of assignments, we sat down and planned. That said, there were no battles fought with flying memos, no flurries of emails, and no two-hour meetings. What we did–what has to be done–was to sit with a pen, paper, three minds, and the list of tasks at hand.

There is a giant whiteboard in the hall at CastleWave. Ron has a big one in his office, as does Rich (not to mention Rich’s little one on the other wall). There is planning software, people who work on planning, and notepads and Post-Its galore. With all of this potential for planning, how do things move forward? Simple: by prioritizing. “It’s so easy to get caught up in all the superficial things,” Rich says. The fluff has to be cut, and it has to be known to be cut. ”It doesn’t matter what mechanism–Palm Pilot, task manager, Franklin Covey, whiteboard–do it weekly and daily, if needed.” Overplanning is dangerous, but not planning can be even worse. The whole purpose of these tools is to know what needs to be done when, and what fluff needs cutting. That sort of planning empowers you. It makes tasks happen.

“It’s important that you get them out in front of you,” Ron adds, “so you can say, ‘Yeah, that’s it, I’ve got them all. I’m considering everything, seeing the full picture, and not just running after something without consideration.” In their book, Get a Life, Rich and Ron talk about something called the 80/20 principle. “Twenty percent of the effort always yields eighty percent of the results,” Rich says. “The trick is identifying the twenty.”

Young startups need life to roll forward. Life isn’t found in carefully orchestrated and thought-experimentally-tested business plans; the juice for bootstrapping comes from cash, action, and customers. “Do the things that bring the biggest fruit first,” Rich says. Brainstorming, whiteboarding, planning, pow-wowing–each of these means the same thing. You have to find what brings the biggest fruit. You do what I did with Rich and Ron. You sit down, create a task list, find the crucial twenty percent, and set your priorities from there. Nobody will be judging your business plan before permitting you to enter the entrepreneurial scene. Good, old-fashioned bootstrapping is only good when the boots fit the foot and the foot starts walking.

Rich closed his thoughts on this by talking about quarters in a Coke machine. If you’ve got four quarters and the first one doesn’t bring anything from the first machine, you don’t stick the other three in three separate machines. You feed that first one until it pays out. Prioritizing is a must. “Lots have written and talked about it,” Ron added, “but boy, it’s even more critical nowadays.”

In my life, I have got to know what constitutes my twenty percent. With everything I get up to, I would be helpless if I went in firing blindly. Poring over trivial details would be just as crippling. When you look at Rich and Ron (or any bootstrapper) and throw in their added responsibilities–family and full-time work leap to mind–it’s no wonder that they are adamant about this principle. Going through eighty percent of the motions does nothing for the momentum. Twenty percent of the effort yields eighty percent of the results. No matter how fast the world is moving, finding your twenty keeps you on pace. Perfection is nice, but success is better.

Bootstrapping my freelance writing career took (and takes) just as much genius, grit, gusto, and gumption as bootstrapping a business. In their upcoming book Get a Life, Rich and Ron call this having a “fire in the belly” and “nerves of steel.” Don’t worry if you weren’t born with those. I wasn’t. There’s no fire until you light it, and there’s no steel until you forge it. Once you get to work on a dream, genius, grit, gusto, and gumption are sure to follow.

Genius has nothing to do with your IQ, GPA, GMAT, or even the New York Times crossword puzzle. Genius is taking a good idea and creating something. Whether you came up with it, caught a wave, or picked a brain, having the idea and taking ownership of it is what makes it genius. Once you’re willing to work at it, time, effort and a little luck will allow it to fall into place. My genius was no different than yours. I had an idea. I owned that idea. It was my dream: pay my way through school as a writer.

Genius does you no good without grit. Simply having an idea is no excuse to quit your day job, so you have to buckle down and work. As a student, my “day job” involved not only classes but also a custodial position. I needed money. I was already working hard. In the face of all that had to be done, it might have been easy to give up on the dream, or at least shelve it for a more convenient time. That’s where determination came in.

More than just determination, though, bootstrapping takes a special fire. It takes gusto! This is your dream that we’re talking about; imagination is no good if it stays inside your head. You don’t buckle down to just stay put. No amount of resolve would have done me any good unless I moved forward with all my heart and soul. Building your idea is exciting! Enjoy it. True, dreams are a tender thing, and so is the heart. It may be safer to put only part of it in, but no half-hearted genius ever realized his dream. You’ve got to light the fire.

Forging nerves of steel is different from having grit. Grit gets you going, in spite of opposition; nerves of steel keep the momentum, in spite of fear. This is the gumption I mentioned. It’s not brainless courage or stark raving foaming-at-the-mouth valor. It’s okay to have a little fear. Bootstrapping will be terrifying. It will hurt. Your heart is on the line. Nerves of steel allow you to see the initiative, forget your fear, and take it anyway. It was scary for me to press “send” on my resume, but it would have been scarier just to leave my heart out there without gumption to back it up. Instead, I am living my dream. Genius, grit, gusto, and gumption grow your venture and they grow your soul. Go on—light the fire. Forge the steel.

However I ended up with my brain, the punchline is that it’s the only one where I’ve got full insider access. I know its informational and creative limits, and I’ve got a rough idea of what I can do before it just shuts down. Here is the neat thing about that: knowing your limits means that you know where you can stretch. Even so, all that stretching can get tiring, and with me being new to firsthand entrepreneuring, my recent mental calisthenics could have worn me out except for one skill. I learned to pick a brain.

This exercise of picking from other people’s brains recently helped on a project from Rich and Ron. They wanted me to write content for a website about cats. Now, I love cats—my ex-girlfriend had several and I never sneezed around them—but deep in my heart, I’ve always been a dog person. That said, it is about seventy-three goldfish, five rabbits, and my ex-girlfriend’s three cats later that I am still dogless. That, and my only firsthand experience with pets was with those to whom the word “personality” applied about as well as Scotch tape applies to wax. (Fish and rabbits are as personable as carpet.)

I worked on the project a while under mere creative willpower. Cats, after all, are just cats—right? That question and others (“Do all kittens sleep all day? Are hairballs indicative or personality or just hygiene? Are black cats naturally more sinister or is that just Hollywood?”) eventually prompted me to do some brain picking. Picking a cat brain might have been pretty effective, but with the inherent communication issues, I settled for a couple of cat lovers.

First up was my lifelong friend Cameron. (We grew up in the same neighborhood.) While I had done some cat sitting for them, his family’s cat experience was even more extensive than mine with goldfish. To me, it seemed like the cats acted differently each time I saw them. Maybe they just knew that I was a dog person. Armed with my concerns, I went to Cameron, making assumptions, hazarding guesses, and drawing conclusions. He agreed with some and discarded others, but what I took in as unformed creative sludge came out with purpose and direction. This taught me two things about brain picking, and the first was the importance of that initial creative willpower. The second realization was simply this: no matter the subject, you probably know someone who can give you a lead.

The experience with Cameron so emboldened me that I went to my ex-girlfriend for her insights. Her responses lined up with Cameron’s. Not only was the cat site approaching authenticity, but I had mastered my brain-picking abilities. I discovered that people will talk if they have a passion for your subject. Their ideas will feed the process you’ve begun and you can keep checking sources until it all falls into place. I started with my idea and got everyone I could to talk to me. Cameron and my ex didn’t grant me full insider access, but that’s okay. I had that in my own brain; their advice just greased my mental gears. It doesn’t really matter, then, that my brain’s the only one I’ve got. There are others out there to be picked.