Bill McCloskey

Serial Entrepreneur
6 minutes reading time (1236 words)

How to Quit Your Job, Be the Boss, and Start Your Own Thing

I’ve been writing about Digital Marketing for over 20 years, starting in the mid 90’s when my columns on 3D Animation on the Web landed me a job as Silicon Graphics World Wide 3D Evangelist. While at SGI, I helped develop some of the first “rich media” banners and went to write articles on Rich Media Advertising for publications such as Clickz and Mediapost.

But starting around 2003 I pitched the editors of Mediapost on a column idea I had come up with called The Email Insider. The column took off, eventually spawning all the other “Insider” columns Media Post launched, and for years I wrote every week on Email Marketing. And I’ve been writing and publishing literally hundreds of articles on Email Marketing ever since.

But lately, I have a growing interest in writing about other topics that interest me. So starting this year, I’ll be writing a series of articles that focus on my “other” love: Entrepreneurship (and other topics that interest me).  I’ll also be asking other Entrepreneurs to share their journeys.

Don’t worry, we will still be publishing thought leadership pieces, reviews, and tactical information to make you better email marketers, but I hope my readers will enjoy taking this ride with me as I expand the subject matter OI covers particularly those of you just starting your careers who hope someday to launch your own businesses.

So let’s get started.

Let’s first talk about age: you can start a company at any age. I was 46 before I launched my first successful company, Emerging Interest. My most recent company, Only Influencers, was launched when I was 56: so First Rule: Age doesn’t matter.

Well: what does matter? Here are the top things you need, in my opinion, and I wouldn’t launch a company without them:

  1. Domain Expertise
  2. A Strong Network
  3. Runway to get to profitability
  4. An idea
  5. Ability to Sell

Domain Expertise

Domain Expertise is being a subject matter expert in your area, or at least perceived as such.  One of the top questions people on entrepreneurial forums ask is: "How do I get an Idea for a sustainable business". When you are a subject matter expert, it is easier to recognize unmet needs that need filling in your area of expertise, which is the basis of a good sustainable and profitable business. Knowing more than the next guy not only gives you an edge from a competitive standpoint, it is one of the first things a VC will ask you if you decide to go down the VC funding route. (more on this in another article).

A Strong Network

If you haven’t begun to build your business network, start today. Your network is your lifeline to everything you do. Not only do your early customers come from your network (people buy from those they know), but early employees, partners, and folks that will help you with funding will all come from your network. When I raised my A round, it was a direct result of someone in my network making the proper introductions for me.

How do you build your network: Trade shows, conferences, meetups, and even prospecting. Put together a solid Linked-in profile (and use a good picture, not a picture of your logo or a cartoon). List your accomplishments, get people to write testimonials on your behalf, and give testimonials to others. People do for those that have done for them, so make sure you reciprocate. Stay in touch, even if it is a quick note to congratulate them on a new job or promotion or to check in after a long absence. The time you spend on your network will pay off many times over.


Runway is just a term that means: how much money do you have. Today there are many more options when it comes to startup capital than when I was coming up. Kickstarter and other services have changed the game for startups.

One thing I’d suggest though is bootstrapping to get your first startup funds. What I did was take out a line of credit on my house and I also had some savings. Friends and family are also a good source of funding as well.  But at this stage, stay away from institutional investors and VC’s until you have some revenue under your belt. The “valuation” you will get if you already are established will be much greater if you already have a profitable business. Valuation determines how much equity in your company the investor gets, and how much is left to the founders. 

In general, you should have enough funds to see you through a year with no sales.  On my first business, I had access, though home equity loans and savings, to about $200k and I still needed to borrow $40k from friends and family.

An Idea

All Wantrapreneurs think the IDEA is the big thing and are often afraid to talk about their idea with anyone without lots of non-disclosures in place. This is the number one mistake people make.  Experienced entrepreneurs know, it ain’t the idea, it’s the execution.

Much more important than an idea is the Barrier to Entry. And being First To Market is not necessarily a good thing. In a future article I will go into great depth on how to validate your idea, and the process you need to do in order to perform the proper due diligence, but for now, remember this: you should talk to who ever will listen to you about your idea, with no NDA’s asked for. Just have a conversation.

The reason no one will steal your idea is, first, people as a general rule are lazy. They have no interest in actually doing your idea  (that you have so much passion for) because it is a lot of work and they would much rather just give you their feedback. Secondly, people don’t steal untested ideas: they steal ideas that are proven and getting traction in the market. They can just as easily steal your idea AFTER you’ve spent the time and money to bring it to market. That is where Barrier to Entry comes in: all great businesses have a secret sauce that makes gives them a competitive edge. That could be data that no one else has, a process that would be difficult to replicate, or partnerships that keep others out.  I’ll be talking more about generating ideas, and the problems with being First To Market in an upcoming article.

Ability to Sell.

Every Entrepreneur that I have ever met is a good salesperson. Usually, they are the Best salesperson the company has. If you really want to succeed as an entrepreneur, learn to sell. I spent years “carrying a bag”.  And I took learning how to sell seriously. I read all the books, no matter how corny they seemed ( a great book is “Shy Salesman have Skinny Kids”), and I learned to recognize the different types of buying signs and purchasing profiles.

Plus I learned the number one rule of sales: LISTEN. Listen much more than you talk. I never did a canned demo in my life.  Everything was done based on listening closely to the potential client’s needs and problems.

That is the end of this week’s article. But tune in each week from now on when we will have a new article on Entrepreneurism from some of today’s best startup founders.



No comments made yet. Be the first to submit a comment
Already Registered? Login Here
Thursday, 26 May 2022