The Blog - Where Business Collides with Human Nature

Multi-hat CEOs


The fewer people you have working for you, the more “hats” you wear.

If there is not enough revenue to support a financial advisor or accountant, one hour the entrepreneur/CEO keeps track of finances and may clean the toilet in the next hour.

This might be irritating? Who went into business to get involved with the “little things?” Wasn’t the objective to make decisions and come up with broad strategies and create success?

The reality is that the best entrepreneurs thrive in a multidisciplinary, multi-hatted role ...but the one-man-band business model limits the potential for success.

Inc Magazine’s article says there are six hats every CEO/entrepreneur wears:

  1. Accountant
  2. Mentor
  3. Sales
  4. Operations
  5. Handyman
  6. Creative

It is impossible to be adept at all. Or is it?


Does a CEO/entrepreneur who ‘does it all’ have opportunity for growth? Yes. But when meeting another CEO/entrepreneur who is also a “one-man-band”, a collision is expected. Both must make a big change. Often, someone “get’s it” and understands that long term success can’t be achieved as a multi-hat CEO. They turn to another who has complimentary skills and talents.

Where can you find such an individual? How can you trust them?

CoFoundersLab is popular. In the room there are cons, predators and wannabe’s. With a little trial & error and plenty of listening, there are gems in the room who have the right character and expertise you are looking for.

Founder2be offers a similar resource.  If you think "dating site", Founder2be is a matchmaker. Sign-up is quick, easy and free. Simply login, complete your profile and you're good to go.

YouNoodle is another popular resource. Startups is their focus. 

FoundersNation is an international resource. There are remarkable entrepreneurs who are passionate and talented around the world. Be cautious. Communication is important. Words have many meanings and different contexts.

Anywhere you see questions and answers is a place to watch people in action. Quora, LinkedIn, Instagram, networking meetups, Reddit, events, award dinners... there is a possibility. All require an introduction and invitation. 

BTW - a cofounder is not limited to only startups. We know multi-hat CEO/entrepreneurs who have operated solo for many years who leaped from a one-man-band with great success.

Taking another look at the list from Inc Magazine’s article, which makes more sense?

  1. Accountant
  2. Mentor
  3. Sales
  4. Operations
  5. Handyman
  6. Creative

The answer varies for every CEO/entrepreneur. Someone with 20 years of multi-hat experience may feel very confident, even regarding their weak areas. i.e. Someone with excellent skills at sales is likely getting by with accounting or handyman activities but maintain ownership over "everything."


Filling in very specific gaps is an option. What are the tasks you don’t want to do, or don’t know how to get done?  After making your list, you can reach out to a freelancer who specializes and offers the right expertise.

Freelancers can be found at, or Amazon’s Mechanical Turk. Fair warning… these folks are often not paid top dollar and may resent it. They may not give you their very best. If you are thinking about a long-term relationship, be sure to send test projects first. After a few test projects, you will have a sense for how they work.


There is a serious gap for most CEO/entrepreneurs in regard to getting more sales. Most get into business underestimating the need or value of marketing and sales. Partnering/collaborating with another CEO/founder or hiring a freelancer who gets paid a commission may be the only way to get more sales. I highly recommend two books:

To Sell Is Human: The Surprising Truth About Moving Others
– by Daniel Pink.

Selling the Invisible: A Field Guide to Modern Marketing
– by Harry Beckwith.

These can help you create a foundation for you and your future team.

If you are hoping to automate the selling process and have several (or many) on your sales team, it is time to think “affiliate system.”

Affiliate marketing is the process of when someone earns a commission by promoting other people’s (or company’s) products. Someone promotes your product to others and earns a piece of the profit for each sale made.

There are many affiliate management systems. Among them are: LinkTrust, Everflow, AffTrack, Hitpath, Impact Radius, Click Inc, and Omnistar Affiliate. They come and go and while there is a price, the time they save allows you to go bigger instead of getting stuck in the weeks.

Outsourcing sales activities (aka Lead Gen Managed Services) is an option. They are paid on performance and will make demands on your team (of one?) to ensure success. Outsourcing sales is not as uncommon as you think. The multi-hat CEO/entrepreneur with a talent to build and serve often miss what it takes to create the sale. Check out Lease a Sales Rep.


Handyman is difficult because in reality, more than one will be needed.  Computer and software repair are essential. “Handyman” for an office can be bypassed if you use co-working place such as InSpark Coworking. They take care of the office essentials, no handyman needed, and a coworking space offers much more.  Office, vehicles, specialized equipment can be critical and if the multi-hat CEO/entrepreneur is doing the maintenance/repair is another hat they must wear, business suffers.


Remarkably, those who are experts and make an impact are not able to turn their knowledge and wisdom into a written format. Writing content that delivers their wealth of knowledge is required. It becomes a sample of their expertise and thought leadership.  There are dozens of online content resources online where freelancers create content and act as “ghost writers.” As with other freelancer crowdsources, it requires a little testing to know who is the “real-deal.”

I find that offers a more realistic/transparent approach to let us know who the freelancers are. If it is difficult to decide who’s best, check out LionShark and let her know I sent you. You won’t be sorry.

By the way…
Do You Like to Talk vs Write? Hire Someone to Transcribe the Audio!

Breaking Away

Breaking away from a multi-hat CEO/entrepreneur happens one hat at a time. There is a risk of creating a Frankenstein operation as each decision to remove a hat can be out of sync. The result can be a dysfunctional team and system. Those with less experience will benefit from an advisory board, a five-star lunch, a business consultant (or mentor), or participate in a mastermind group. This is also where a less experience CEO/entrepreneur would gain from a savvy-experienced “cofounder.”

What is an area of low expertise? … or when are you unwilling to do the work?  (Which leads to avoidance.)

It is time to start interviewing. Help is likely to come from someone you have not yet met. Every new conversation can (and should) be an interview. (for both parties)

Topics: Entrepreneurship Entrepreneur