Actionable Business Problem Solving Advice From a Serial Entrepreneur

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As your business grows you’ll have to deal with more problems. Also, the problems you’ll face don’t get easier. They get a lot harder, a lot bigger and a lot more complex, therefore your business problem solving skills need to continually improve.

On the positive side, as you start building out your team, you can delegate solving business problems to them.

You can’t delegate everything, but you can delegate most things. It’s really your ability to handle and solve complex and difficult problems that will make you or break you as your business starts to scale.

My Experience Solving Complex Business Problems

Business Problem Solving Skills

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Over my 20 year career as an entrepreneur I’ve built 8 companies (which have generated over $250,000,000 in total sales) and I’ve had to deal with lots of really big, scary and even upsetting business problems.

I’ve lost an employee to cancer. I’ve had a mentor commit suicide. I’ve had to raise money in a down round, because my business wasn’t doing well (and we were desperate for cash). I’ve even had an assistant steal $50,000 from me.

Maybe the hardest business problem of all was coming close to selling one of my companies for $650,000,000 USD, then having one of my investors f*ck up the deal at the last minute.

You sure build a thick skin when one day you’re planning how to spend $100,000,000+ and the next day the deal is in the toilet.

These are the kinds of business problems that I’ve personally had to solve over the last two decades. In a perfect world there would be no problems to solve when building a business, but you and I know that’s never the case.

The good news? Solving these problems has allowed me to build multiple successful businesses. I’ve travelled the world. I’ve met my heroes and idols. I’ve played basketball with John Wall and Bradley Beal from the Washington Wizards (I’m obsessed with the NBA). I’ve sat courtside for more Lakers games than I can count.

… but most importantly, I’m providing jobs for hundreds of amazing people.

How To Get Better At Business Problem Solving

I’d like to give you three tips that will help you get better at solving business problems, because if you haven’t had any major problems in your business  yet, then unfortunately the bad news is you will.

It’s only a matter of time.

Now I say that not to be a pessimist. I am an optimist. Anyone who knows me knows that. But let me be real — you will get challenged. Problems will come along and smash you in the face, trying to get you to quit. To resign, To give in.

It’s how you deal with those problems that will make or break you and your business.

Business Problem Solving Tip #1: Tackle The Hardest Problems First

Business Problem Solving Hard First

Let me be brutally honest — you need to tackle the hardest problems in your business RIGHT NOW. Stop letting them linger because you’re too scared to take action.

For example, if you need to fire someone and you’ve been putting it off, then just go and rip the band aid.

Do it today. Don’t delay it any longer. Call a meeting with that employee NOW and get it done. Seriously, go. Stop reading this post and do it now.

I’ll wait…

If you can’t handle firing someone, then you’ll never be able to handle the bigger and more challenging problems that will come your way as your business grows, such as legal issues, competing for talent, being sued, raising money from investors and building a great management team.

The lesson? Take care of the hardest problems NOW, before they becomes catastrophic problems and start having a measurable impact on your business.

Business Problem Solving Tip #2: Hope For The Best But Plan For The Worst

Hope For The Best, Plan For The Worst

I’m always focused on doing whatever I can to make sure things go well, but at the same time I’m a realist. After building businesses for 20 years, I know that most things won’t go exactly as I’d hope for.

As such, I’m what I call “pessimistically optimistic”. I hope for the best but have a contingency plan in place if things don’t go exactly as planned.

In practice, that means I create three growth forecasts for my business:

  • Best case
  • Worst case
  • Probable case

The best case plan is exactly what it sounds like. If everything goes perfectly and nothing goes wrong, then I expect to end up in the best possible position.

The worst case plan assumes most things will go wrong. This is the plan I run my business by — but I keep this plan to myself and only act on it if something goes wrong.

The probable case plan is what I compensate my management team on — and what I share with my investors. It assumes 80% of things will go according to plan while 20% won’t.

The best thing about planning for the worst case outcome is that you start asking yourself (and your management team) smart questions, such as:

  • “What should we do if we can’t hire a great CMO?”
  • “What is our plan B if we can’t raise money from investors?”
  • “What happens if our new marketing campaign flops?”

These are the hard questions all great CEOs contemplate. When answered correctly, they will allow you to not only deal with tough business problems, but swiftly move past them.

Business Problem Solving Tip #3: There Are No New Problems

Business Problem Solving No New Problems

One of my earliest mentors taught me that there are no new problems, because every problem you’ll experience as your business grows has already been solved by someone else.

Re-read that last sentence and really let it sink it. It’s important.

Your job then, is to find people who have solved the problems:

  1. You’re experiencing and
  2. That you WILL experience

These people can come in the form of mentors, coaches, investors, advisors, founders, etc.

The easiest way to find people who can help you solve complex business problems is to simply reach out to them. LinkedIn is a great place to start.

Ask yourself who has built the type of business you’re aiming to build, then start searching for them on LinkedIn.

When you find them, connect and send a personalized message asking how YOU can help THEM. Not the other way around.

Always aim to add huge value FIRST, before asking for help.

Also, try to take the conversation offline as quickly as possible. Get on the phone, meet for coffee, buy them lunch, etc. Face-to-face is best and will allow you to build relationships quickly.

One of the first things I always advise first-time founders to do is build an advisory board. An advisory board is a group of experts who can help you navigate the challenges of growing your business with fewer mistakes and more confidence.

You meet with your advisory board once per quarter (and via phone in between meetings on an as-needed basis) and discuss the challenges you’re facing as a CEO.

Whenever I start a new company, I don’t focus on building the product first. I always build my advisory board first and THEN think about how I can solve a problem in the market I’m focused on.

That’s It…

Those three deceptively simple tips have allowed me to build multiple successful businesses, raising over $100,000,000 from investors and hiring almost 1,000 amazing people over the last 2 decades.

Which tip have you found the most useful? Comment below and let me know!

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