Entrepreneur Home Office

Show Notes: Hang Out A Shingle

(UPDATED 2020-07-2020)

The following list of notes, links, and resources complement the Hang Out A Shingle – Starting Your Cybersecurity Company webinar featuring Daniel Ayala and Douglas Brush which can be found on the Denver ISSA YouTube channel

While we titled the talk as a focus on cyber and information security, there are some fundamental resources you should work through when considering a start-up or entrepreneurial endeavor. 

Why am I starting a business?

20 Right and Wrong Reasons to Start Your Own Business

SWOT Analysis: SWOT analysis is a strategic planning technique used to help a person or organization identify strengths, weaknesses, opportunities, and threats related to business competition or project planning.

Addressing Business Skills

Leaders vs. mangers: Leaders have people who follow them; managers have people who work for them. Leadership tends to be more strategic (e.g., looking at the horizon), and managers tend to be more tactical (e.g., looking down).

The Entrepreneur Myth (“E-Myth” by Michael Gerber)

If your business depends on youyou don’t own a businessyou have a job. And it’s the worst job in the world because you’re working for a lunatic!”

Business Plans

Mission Statement

Answer the question: “How will I know when I have succeeded?” 

If I Read One More Platitude-Filled Mission Statement, I’ll Scream

Writing Your Plan

Paying Yourself

Metrics & Finance

Corporate Structures

Choosing a Corporate Structure


LLCs have become an easy and efficient way to start many companies. There are pluses and minus to this structure, but it is something that most people can file themselves. For LLC registrations, you perform a name check, submit articles of organization, pay a fee, and you are off to the races. 

After the LLC is formed, you can and may have to get an Employment Identification Number (“EIN”) from the Federal IRS.

Planning, Strategy & Marketing

Lean Business Planning

Enterprise Operating System (EOS) & Traction



The best tip we can provide: Give to get. Don’t go for vanity metrics like site visits, likes, impressions. Build evergreen content on blogs, podcasts, YouTube, webcasts, etc., which contribute something meaningful to your die-hard early adopters (see 1000 True Fans).

Solve problems and then socialize them via Facebook, Twitter, LinkedIn, Reddit, or wherever your 1000 die-hards “waterhole.” They will then, in turn, promote you. This gives you the most stickiness to your early customer base. Additionally, this material can be repurposed and referenced over and over again due to its contributing value (hence “evergreen”). 

Focus on evergreen content development first to build your brand. Then focus on other industry contributions such as speaking engagements, free tools/software, etc., keep giving to get.

A start-up marketing strategy should cost time more than dollars. When you are ready, you can then build marketing strategies where you can spend money on ad-words, inbound campaigns, press releases, and conferences. Don’t burn these dollars until you have a brand built on reputation. This is the single biggest pitfall start-ups make.


Board of Directors


Advisors are a great way to gain insight and expertise. Generally, these advisors are “paid” in preferred stock or a position in the new company. This is an excellent way to fill gaps in your knowledge or network with relatively low costs. However, it is essential that the advisor relationship is well-vetted (legally and financially), and there are clear expectations and milestones for all parties. If you are name dropping headshots for your website to build our advisor “About Us” page, you are doing it wrong. Make the relationship transparent, accountable, and tied to measurable KPIs.

Additionally, your advisors need to call you out on your BS. You don’t want an echo chamber. For useful insight on how to surround yourself with advisors, Google “how President Lincoln built his cabinet by filling it with his rivals.” Avoid your cognitive biases as much as you possibly can. 

When to Exit (Bye Felicia)


Imposter Syndrome

Biases – Sunk Cost Fallacy (aka Gambler’s Dilemma)

Biases – Bike Shedding

Biases – Confirmation

The Taxman Cometh

Note/disclaimer: Get competent tax and legal advice early in your start-up process. This is an overall guide, but not in any means meant to be tax or legal advice. Google ‘till your fingers hurt, take notes, then talk to a licensed professional. Missteps on taxes can really cut into your operating costs when you suddenly have to pay taxes + fines + interest because of a misfiled or overlooked form. Calculate professional service fees into your start-up costs as they are far less than the burden of a mistake which can cost far more, hurt your credit, and incur legal fees if you do not do things the right way.

Final note: learn sales tax regulations. This is a messy area, even for the most seasoned business owner and tax preparer. Services and products are taxed differently per state, per county, per city (fun!!!), and a mistake here can result in hefty fines and loss of a sales tax certificate, essentially shutting down your business. 

Also, recognize that bookkeeping and tax preparation (accounting) are two sides of the same coin that do not fully equate to each other. Bookkeeping is there for you to have the tactical insight into your cash flow and does not always relate to a line item on a tax schedule. Additionally, depending on your corporate structure, not every dollar is yours or the company’s depending on how the funds are reinvested, the number of shareholders, and how your specific structure and business needs calculate profits and losses. 


Take all of these with a grain of salt. These are here for reference purposes and do not constitute an endorsement, or legal, tax, or business advice. Your mileage WILL vary. Do your research, ask questions, and compare alternatives.

However, avoid analysis paralysis. Create rubrics that allow you to evaluate selections with weighted ratings to prevent bias.



Some will also offer payroll services. You also MUST know the difference between W2 employees and W9 contractors!


First, understand the various coverages you might need for you and your business from cyber, E&O, general liability, business interruption, disability (short and long term), workers’ compensation, health, etc. Then, work your network to find brokers. Brokers work for you at no charge to you. They are incentivized to place you with the best coverages which will renew year after year, even if you have claims (a.k.a. retention). They often have a lot of material they can send you, which will help you in the underwriting process and can answer a lot of questions about what you need. 

Cloud Tech – Desktop Apps (SaaS)

Cloud Tech – Infrastructure (IaaS)

Co-working Spaces

Business Accelerators

Virtual Assistants


Start-Up Schools

Networking and Speaking

1 Million Cups

1 Million Cups (1MC) is based on the notion that great ideas are discussed over a million cups of coffee. 1MC is not a pitch platform, nor is it a networking event. It’s simply a chance for 1-2 presenting entrepreneurs to tap into the knowledge and experience of the local community in a focused and encouraging environment.


Toastmasters International is a non-profit educational organization that teaches public speaking and leadership skills through a worldwide network of clubs.


Meet-up is a bit of a catch-all for various networking and meet-up groups. Spend some time looking for events in your area that match your business need. If you can’t find something, start one! This has been a very effective free growth strategy to promote yourself as an influencer and community leader.


Start-up Podcasts

Business Books

Reading is fundamental. These are books we found critical in our successes (I recommend reading in the order listed as they build on each other and have a compound effect. – Doug). Some of these are tactical and actionable, and others develop a mindset. This is not an exhaustive list, so find what works for you to build a vision, processes to support that vision, and a way to then step away from the business as fast as possible. You want to build towards simplicity and automation. Process flow your operation. Eliminate yourself from every box in the flow where the “factory” stops because you are personally needed to make a decision. 

Success is a business that can run itself and you are not essential to operations.

“I try to invest in businesses that are so wonderful that an idiot can run them. Because sooner or later, one will.”

Warren Buffett

Tooltip! Check out Readwise –  It’s a bit of a productivity hack as well.

Readwise fixes this using a scientific process called Spaced Repetition. We surface your best highlights back to you at the right times, and let you review them every day with the daily email and app.

This application will send you your highlights in books you read on Kindle (honestly, the best way to read the books recommended so you can highlight and search later). Audiobooks and summary services (see below) won’t work with Readwise, obviously.

Time Management and Efficiency Resources

Time is your most valuable commodity and asset. Don’t you (or let others) waste it. 

You cannot earn or manufacture more time.

“People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully. I’m actually as proud of the things we haven’t done as the things I have done. Innovation is saying no to 1,000 things.”

Steve Jobs

Time Management – What gets measured, gets managed. How much of your time is being dedicated to specific tasks? What if you could measure what you do and adjust to get the most out of each hour (time arbitrage: not every hour of the day, has the same value or output, for different tasks). 

RescueTime: Automatic time-tracking, distraction blocking, and more! See exactly where your time goes, block your worst distractions, and get powerful reports and tools to improve every aspect of your day.

Productivity “Hacks”

The Art and Science of Learning Anything Faster

“If effectiveness is doing the right things, efficiency is doing things right.” 

Tim Ferriss

Content Summary Services – Cliff/Spark notes for business books. We are not going to lie, so many of the books we read and recommend can be trimmed down, but then they probably wouldn’t sell as books. Advantages are you get the essence of most. The disadvantage could be knowledge retention. Some of these also have audio synopses.

Speed-up play on YouTube videos, audiobooks, and podcasts

Audiobooks – Audio books are great ways to digest many of the books recommended, particularly if you commute or travel (ditch the news and drive time radio. Feed your brain instead). Additionally, with Amazon and Audible, many audio books come included with the subscription service.


“You can fail at what you don’t want, so you might as well take a chance on doing what you love.”

Jim Carrey

A few choice inspirational videos on life and business

“I can buy anything I want basically but I can’t buy time.” 

Warren Buffett
Audio Conferences Home Office Remote Video Conferences

Tips for Online Meetings

This was written by a colleague of mine, Katherine Ball, and shared with me. Katherine has graciously allowed me to share this on Smartly Remote.

I put together the following text to share with online meeting participants for groups I am a part of and thought others might like it as well. So, here it is…

Pointers for Meeting Online  

Virtual meetings are to be conducted like face-to-face meetings; allowing interaction during periods set aside for input, questions and answers or by raising of hands to indicate a need to interject.

Role of the Moderator  

  • The moderator’s role is to help maintain control of the virtual room by interjecting as needed.  
  • Please be patient with individuals serving this role as they may need to adjust talking points during speaker pauses and transitions and guide discussions, remind speakers to repeat questions from attendees before answering them, and/or call on people notably quiet throughout the meeting to be sure everyone has an opportunity to voice their thoughts.  

Role of Participants  

  • We strongly encourage the use of video cameras so everyone may benefit from reading non-verbal communications.
  • Try not to multi-task.
    • “Because of the interactive nature of this meeting, it would be best if we could have everyone’s undivided attention. As such, we hope you can avoid checking email or entertaining other distractions. Feel free, of course, to take notes.”
  • Avoid over-talking, miscommunication and the potential for diminished sound quality.
    • “Please mute or turn off devices.”
    • “Please speak clearly into a microphone/headset when possible.”
    • “Raise your hand in the camera, use “raise hand” features or send a message using the chat or other messaging feature of the tool (Teams, Zoom, etc.) to indicate you would like to speak.” 



Just a quick welcome post as we kick off Smartly Remote. This idea came from a group of people who wanted to bring our significant collective experience in working remotely to those that might be encountering it for the very first time, either by choice or by necessity.

We will have a number of content posters on the site so we hope to bring a lot of diverse views on the topic. There will be blog posts with information on specific topics, a quick-read FAQ that will get new people started on working remotely, and a list of links to great articles we have found to help further the discussion.

Welcome, and enjoy! It’s time to work remote and do so smartly.