These Two Issues Cause More Business Headaches Than Anything Else

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During interviews, serial entrepreneur Elon Musk will often reference the fact that running a business is primarily about “solving problems.” Every day, there’s a new challenge to overcome. 

But, as he rightly points out, there’s a big difference between a challenge and a headache. A problem is something new and unexpected – something that emerges from the general chaos of the universe. A headache is something you know is going to ruin your day. 

In this post, we’re going to take a look at the two issues that cause more headaches for entrepreneurs than anything else, and what you can do about them. 

Your IT Systems

The value of IT networks is so extraordinary that practically every business now uses them. They offer instant communication, productivity apps and tools for product development. 

But when you think about it a little more, this setup strikes you as rather odd. IT networks are highly technical and specialized systems requiring expert knowledge to keep them operational, yet even the smallest of companies must somehow run their own. In other words, IT demands extensive expertise, but few businesses have it. 

Interestingly, this doesn’t happen in any other areas. Almost all companies, for instance, hand over their accounting to a third-party agent who does it for them. The same often applies to marketing too. Entrepreneurs understand what they can do and what they can’t. 

But when it comes to IT, there’s a feeling that it should all be managed in-house. Entrepreneurs are prepared to put up with the endless compatibility issues and downtime because they believe that they have no other choice. 

Of course, none of this is true. Businesses can wholly outsource the management of their network to third-party providers, negating the need to struggle with issues. You can get more details on this with a simple internet search. But the bottom line is this: the moment you hand over the job to an agency, all your issues will evaporate. 

Your HR Management

Business owners often say that doing business is easy – it’s managing people that’s hard. 

In many ways, this is true. Employees can create all manner of problems for management and, in some cases, put company operations at risk. 

The trick to solving this problem is to implement better HR practice, but how?

The first tactic is to upgrade HR software to make managing things like holidays, payroll and sick leave easier. Relying on spreadsheets is not a good idea. 

The next step is to get everyone in your organization on the same page. Each member of your team should have a clear and well-informed idea in their heads of the overall goal and mission of the enterprise. What you don’t want is people working across purposes, with some going in one direction, and others going in another. That’s not good. 

Finally, you need an HR setup that allows you to find the right people for your organization. Recruiting should be a priority from the outset, not something you leave until you have no choice but to make additional hires.

Working With Others Without Losing Your Business

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Veteran business owners will often make the recommendation that you should avoid running a company with people you care about. Friends, family, and your special someone are all prime candidates for the sort of person you’d want to work with, and you probably already admire a lot of their qualities. Unfortunately, though, running a business with people like this can be unnecessary stress on your relationship with them. To help you out with this, this post will be exploring some methods which can be used to ensure that your business doesn’t get in the way of the people you love.

Two Businesses

Some of the world’s strongest business partnerships have been those which have originated from the same group of people. Having already broken the ice a long time ago, negotiating with people like this will be easier than doing it with anyone else, and you can build two businesses which work in harmony with one another. This leaves both parties free to get on with their own  work, while also taking away the reliance you have on one another to make money. There are few things worse than having arguments because one person can’t work as quickly as the other.


Persuading someone to start their own business isn’t always the easiest idea, but may mean that the other side of this arrangement isn’t unhappy with the idea of not owning a business. In this case, you could work together as subcontractors, with you passing work down to your friend or family member in the form of freelance work. You will need to manage the legal side of this, with options like CIS registration making it far easier to handle payroll and taxation. Along with this, you will also need to make sure that they are aware that this work may not be permanent. If you can’t get work, you won’t be able to pay them.


Finally, if the idea above don’t work out, you could think about the idea of simply employing the person you want to work with. While this means they will have less freedom, you can offer them a profit sharing clause in their contract. This means that they will still benefit from making the business grow, but will also have the freedom to move on in the future, without forcing you to find ways to fill in the gaps while they still own part of it. Employing someone is a complicated process, and you will probably need help along the way. A dedicated HR company is usually the best option for this.

Hopefully, this post will push you in the right direction when it comes to working with the people you care about. A lot of people think that their relationship is too strong to be hurt by something like this, but there are few things worse than not being able to meet each others expectations. It’s best avoided, and there are some easy ways to achieve this goal, making it worth putting effort into this as you begin to grow.

Winsight Episode 21: Recipe for Success

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If you’ve read business books, online articles or things of that nature you’ve heard inspiring stories of successful business ventures gone right. What you don’t realize is that represents about 1% of what business owners really experience. I mentioned in a prior episode that the fail rate for a first time business is 80%. Those are the statistics that don’t get publicized because it doesn’t “sell” well.

What you should really be taking a closer look at is a successful serial entrepreneur. Someone who has taken his/her formula and plugged it into several businesses over and over again with positive results. The business (or the product) gets the glory, but the recipe for success is actually the process repeated.

In this episode, I’ll share the following examples:

How Terry made the transition from real estate to restaurants seamlessly

What a special recipe and unique selling point have in common

How we think of businesses “backwards”

The role of a system and how it can transform your business

After listening to this episode, what ingredients are in your recipe for success? Has your focus on your dream changed? If so, how?

Winsight Episode 19: Buffet Strategy

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Remember the last time you ate a buffet? Your first trip is laced with excitement seeing more things to try than your stomach can handle. You put several different kinds of food on your plate because you want to try the various tastes out. Some of the items you like, but some things you don’t. It’s the second and following visits back to the buffet where you weed out what’s good and what’s not. This experience is relatable to entrepreneurship. If you’re a current business owner or an aspiring one, listen up because the buffet strategy is important to you.

In this episode I will discuss:

  • Why serial entrepreneurs are better than one-time entrepreneurs
  • Why the “system” may matter more than the industry
  • What a buffet and entrepreneurship have in common
  • The one factor separating you from being a business owner

Are you a current or aspiring entrepreneur? (Who doesn’t want to be their own boss?) What do you know about entrepreneurship? What lessons have you learn through entrepreneurship? Please share your comments below!

Winsight Episode 4: Successfully Failing



A successful failure? Seems like an oxymoron huh? But actually it’s not.

In this episode learn how failure is essential to success. Here is what is covered:

  • Failure is simply a numbers game. Learn how to play it and win.
  • What a baseball players batting average has to do with your success
  • The myth of risk and why resting your past successes is a recipe for disaster
  • Insanity, growth and what regret can do to your soul

How willing are you to fail? Share your number and why you chose it below. Remember transparency is part of growing.

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Q & A w/ Serial Entrepreneur – Gail Cayetano Classick

I met Gail in 2011 through a mutual friend who insisted that I had to meet her. My first impression upon meeting her was ‘I’ve never met someone so nice AND business-savvy.” After briefly talking, I continued to keep in touch with her and eventually coaxed her into speaking at my network event. I’ve witnessed her successfully launch and run several businesses and continue to be impressed at her drive, execution and personal touch. Get ready to soak up some wisdom while reading her answers! In fact I’ll be hosting The Secrets to Entrepreneurial Profitability with her a week from today in Santa Monica. Get your tickets here!

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1) What’s your drive/motivation as a serial entrepreneur? 

I enjoy building things from the ground up – my approach to anything is I put my head down, work hard, and don’t come up for air until I know I have a business that is sustainable.  Looking back on my life I’ve always been the one to start or lead things from an early age, whether it was the new club at school, a new approach on how to fundraise for a nonprofit, or coaching a team that could use the help.  That internal motivation is something that naturally permeates into all aspects of my life.

2) What has been the ‘common thread’ of success with your 3 businesses?

I know I am not an expert in all aspects of business, and realizing that from the get-go has enabled me to build strong businesses by forming partnerships with others who are much more knowledgeable, successful and interested in those parts of the business than I am.  I stick to what I know I do well (typically marketing and business development) and leave the rest to the experts in the other fields.  These types of collaborations have catapulted the growth rate of any business I’ve been involved in.

3) Most entrepreneurs are passionate about their idea, but how do you make the transition of turning your hobby into a business that makes money?

For anyone starting a business they need to realize that they can have the best, most unique, top-of-the-line product or service out there, but if they don’t know how to go out and make money, then their hobby isn’t a business.  No one (well, almost no one) likes to go out and try to make sales happen (not even me), but if you’re not willing to go out and ask for the sale and overcome those fears, then you won’t be able to make a living.  If you really, really, really don’t want to go out and sell your product or service, then you will have to hire people that can do that for you, and manage them well.

4) When it’s all said and done, what type of impact do you want to leave on people?

I don’t need to be famous for some groundbreaking new approach or business (I actually hate being the center of attention), but if the way I do business can inspire someone else to live out their dreams like I have, then that would make me happy.  I want someone to look at what I’ve done and push forward with their ideas because they know that if a regular person like me can do it and make an honest living, they can too.

5) What’s one piece of advice you want to give fellow entrepreneurs? 

If you’re going to fail, fail fast.”  That’s one of my favorite sayings and I believe I truly operate that way.  The business world moves so quickly nowadays that you need to hit the ground running.  If you are starting a business, YOU are setting the pace of the company.  YOU are.  Not anyone else – not the industry you’ve chosen to be in, not the circumstances surrounding you, not your staff.  What’s worked for me is allowing myself and my team to take risks and make mistakes, as long as they don’t spend days/weeks/months agonizing over whether they should even try in the first place.  I want people to learn, to try, and to move on quickly if it doesn’t work out.

Gail Cayetano is the Co-Founder of Starfish Creative Events, a full service event marketing firm formed in 2008 that specializes in events and promotions for corporate and entertainment clients (including Sony Pictures Entertainment, Konami, Virgin and Namco Bandai), as well as CEO of Shop Talk Los Angeles, a strategic partnership consultancy for mid-to large- sized businesses (clients include Hasbro, Boston University, Warner Bros. and Tweak Footwear) formed in 2011. 

Most recently Gail has teamed up with her sisters to bring to life Cayetano Legacy Collection, a women’s statement accessories brand whose focus is to collaborate with citizens in the beautiful but third world country of the Philippines, to assist them in gaining additional skills and encouraging economic growth through the design training programs that CLC supports. The goal of Gail and her two sisters Karen and Christine is to provide “hand ups, not hand outs” to the country that has given them their heritage.  

In Gail’s free time she serves as Chairwoman of the Children’s Miracle Network’s Extra Life Marathon and is on the Board of Directors for the Toast Our Vets nonprofit. Prior to her entrepreneurial work and after receiving her BS from Boston University, Gail rose the ranks in the business world with stints at companies such as Activision and Konami Digital Entertainment.  In 2008 she was named The Stevie Awards’ “Best Young Entrepreneur,” 2010 to the Los Angeles Business Journal’s “Twenty in their 20’s” honoree list and 2011’s “Best Young Entrepreneur” by the FAOCCOC.