Ironman: The Business Design Challenge

Boss, Friends, IT Business, SMB

At a recent conference I was asked if I’d consider doing the ironman push again.

For those of you that aren’t devoted Vladville followers, I worked 90 days straight from January 1st – March 31st. No breaks, no vacations, no days off, no Nyquil. It was a brutal schedule that allowed me to break through some crazy personal and professional obstacles and reach new milestones.

I’ll never do that – but allow me to offer some perspective. If you’re squeamish you might want to skip the next section. Scroll down to The Business Design Challenge.


Best job in the business.

Flexible hours, obscene pay, minimal supervision and unlimited opportunity.

Then you kind of wonder how shit like this happens:


To all my friends in business and those who want additional responsibility: be careful what you wish for. While it’s easy to only see the nice parts of the job, there are those emotional aspects of it that you don’t get to leave at work at 5:30. Most employees think their bosses are awful and that work can ruin their day. Then again, most employees can find another job in a few months and they are only accountable to themselves.

Slightly more pressure on the management. You see, a crappy toxic employee not only sucks at their job but also happens to antagonize everyone else they come in contact with – both employees and clients alike. In a way that would affect that business for a while. It’s a domino effect that affects the performance of the entire organization – if the manager has a bad day, so does everyone that works for them. And everyone those people touch as well.

The job of the CEO is two fold – deal with the employees and deal with the customers. Defend your team, listen to your customers. Represent your customers and argue with your team over the right direction of the company. Empower employees while guiding them. Guide them while attempting not to lecture them. Take their feedback while dismissing their concerns and opinions of the overall direction. Line up the marketplace demands with the client expectations with the employees ability to do their job in the goal that the company delivers on it’s promises at a scale that generates a profit.

Oh yeah, try not to offend anyone while doing it.

Maintain composure throughout this process while that nagging little voice of no confidence and risk aversion keeps on whispering: “If you fuck up, you don’t just fail and move on – you affect thousands of jobs, companies and business relationships that have taken a lifetime to built.”

The Business Design Challenge

Every small business owner has an idea and a passion. That’s how it all starts.

After you reach any reasonable level of success the ideas you’ve had as the entrepreneur take on a life of their own, different employees take on the vision and drive the delivery of those ideas and solutions to the marketplace. But because you’re so disorganized and relentless in pursuit of your dream in it’s early stages, little cut corners and “problems that will be fixed later” snowball at this stage: The Avalanche.

The Avalanche: Trouble with problems in small business is that they never get smaller. They only get bigger. And more complex. And involve more people. And require more money. Oh – and end up distracting the whole company to get resolved.

I’ve seen most of my entrepreneur friends crack and burn out in this stage. They either fire everyone around them and attempt to blame everyone but themselves for the issues or throw their personal life in an repairable disarray.

The trouble with the avalanche is that the person that caused the problem must both be strong enough to let those around them in on the issues and help own the problem and fix the solution – while the person also admits they created the problem while showing confidence that they know how to fix it.

Describe the problem. Explain it, solicit input, delegate, lead through the fix.

As the company grows from being a small business / startup mode in which everything goes, growing up takes forever. Designing a large business is not the same as a small business maturing – it’s about sustainability, mentoring, delegation and elevating your game to the next level.

Most people crack here. Personally. Professionally. Mentally. At the end of the day, is all this hassle worth a few more million or am I bored with it?

This is where most small businesses end. Either in a tailspin out of business, or an acquisition… or hopefully something better.

Motivation Process

My Ironman was an admission that I couldn’t deal with the pressure of fixing the problems I’ve caused in designing OWN for a full year that it would take to address them. So personally, I decided I could do it in 3 months if I absolutely focused and did nothing but work. I was right. So here are some tips:

1. Recognize the problem.
2. Admit it’s your fault.
3. Ask others for ideas how to solve it.
4. Ask inside / outside. Employees and clients.
5. Draw up a plan.
6. Sell the plan.
7. Cut the plan up and delegate it all away.
8. Draw up reporting.
9. Design milestones and rewards for reaching them. Start here.

You wanna line up a lot of witnesses to you don’t wuss out. What people often make a mistake of doing is hiding what’s going on – it’s easy to quit when you don’t have a bunch of people that will watch you fail. Call it motivation.

My Challenge

I’ve been fortunate enough to be around some great people while building Own Web Now. I’ve seen some succeed. I’ve seen many fail. Those that flunk out and get jobs aren’t going to be writing books about it. Those that succeed have businesses to run. I on the other hand don’t sleep a lot.

You’re not gonna read a book about it. But boy will you know when the problems you’ve created in your business are bigger than you or your ability to solve them yourself.

My problem was that I had a lot of really wacky ideas that I built into products and services from 2003-2007. Then as the cloud stuff started picking up steam all of my crackheaded ideas turned into big products. Then from 2008 we had to focus on service and grow up fast – away from grunt work of infrastructure and data centers to a mature business model of delivering services. It was a huge transition. And while we figured out all aspects of the business – running a business is more than just making it through the day. That’s business management. Running a business is about taking it in a direction. At the beginning of the year, we had a hustler problem – we could do everything but you needed to know someone. That doesn’t scale. So my challenge has been to document the business, delegate it away and dedicate more of my day-to-day on what the business needs to do next.

I made it through my ironman and my company, my team and everyone we serve is much better off as a result of it. Own Web Now is operating on a different level in June of 2011 – instead of at some point in 2012.

That, I hope, makes all the difference. After all, I now play in the big leagues.

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