Version 1.0 – Updated May 2023

A practical blueprint of all we’ve learned (so far) about how to start, fix, run, and grow from a small business to a medium-sized business (SMB) without losing your mind…

Table of Contents


Preface: This article draws from my 30 years of business experience, with the most recent time spent collaborating with Liza Graves, the founder and CEO of Blueprint.Inc/StyleBlueprint. Liza has always been my most trusted advisor; together, we’ve gained valuable insights. The majority of the mistakes and lessons mentioned here come from my experiences with the first two companies I helped establish and grow. My intention is to demonstrate that it’s never too late to learn and adapt, as we’ve done at Blueprint.Inc. I give 100% credit to Liza for teaching me how to work more effectively with people, as she is a natural leader, which I hope shows. We both are passionate about supporting local businesses and helping them succeed. If the information we share in this article assists business owners, we will have made progress toward that goal.


Either on purpose or accidentally, you now have started, own, or inherited a small to medium-sized business (SMB)! No need to expound on how you got here. Anything from “I’ve always wanted to be an entrepreneur!” to “Oh shit, what just happened?” is possible. It doesn’t matter. You now need to figure out how to keep your business afloat, your customers happy, your team from killing you, and generate profit to reinvest in the business and provide a return to your shareholders (even if that is just you).

There are 1,000 different business coaching methodologies and services. I highly recommend picking one that works for you. However, there are some foundational principles and practical and tactical tools that I’ve found missing from nearly every approach I’ve currently seen. Consider this “Blueprint” a starter kit to get started or to reset your expectations. Warning: it contains mostly tough love. Everything here is based on my almost 30 years of success and failures. If I could go back in time, many of the failures did lead to eventual successes but could have been easily avoided. If one person finds the blueprint instructive, it is worth the effort.

On that note, you don’t have to own the business to find this information helpful. Look at your boss and say, “Look at the dumb mistakes this guy made. We don’t want to do that, do we?”

There are three sections of the blueprint: 1) People, 2) Process, and 3) Tools. This is an adaptation of the quote from Col. John Boyd “People. Ideas. Machines. In that order.” (Also, the inventor of the OODA loop – more on those later.)

I propose a rough formula on how to spend time as a leader based on experience rather than a rigorous review of data: 60% people – 30% process – 10% tools. Another way to say this is you can have the perfect business model and the best tools money can buy, but if you don’t work well with people, you are dead in the water. People are your foundation and will always be the area you spend the bulk of your time (even if you don’t plan on it). If that doesn’t work for you, there are lots of careers where individual contributors can have wonderful jobs and make a lot of money. Business ownership and leadership, however, is not one of them.

We call it the Blueprint Pyramid:

Blueprint Business Pyramid

As you, too, are likely a squirrel-brained entrepreneur, we will reverse the order of presentation. Again, we all should spend most of our time working with people. Based on experience, I am saying this knowing that most people won’t listen, just like I didn’t listen. With that said, the reason for starting with Tools is that tactical things are often easier to digest. They are sometimes stumbling blocks that take time away from the most important things (not to be repetitive – People are most important). So let’s get Tools out of the way quickly and move to Process and People.


Blueprint.Inc | StyleBlueprint

“Men have become the tools of their tools.”

Henry David Thoreau

“If I just get this new piece of software, all my problems will be solved,” says almost every leader in business at one point in their career. It never turns out to be the case. There are no magic beans in life or business. However, some beans work better than others, and you have to have them.

Here are some must-haves to start:

Quickbooks for Accounting

Unless you are in a specialized business with an absolutely and clearly better choice, Quickbooks is your choice for accounting. Period. Every accounting firm supports it. Every other tool plugs into it. There are a thousand training options to learn it and ten thousand people that can fix what you break. Just do it.

As a rule of thumb, Quickbooks is great for $0 up through $5M in revenue. However, I’ve seen it work up for businesses up to $10M without breaking (but that depends on the business and how well it fits the platform). Eventually, you will outgrow it, but it takes longer than you might think. for Payables (and sometimes receivables)

This is the best tool for handling the bills you need to pay. “Bill”, as they like to be called these days, virtually automates paying your vendors and, used properly, keeps your business safe. Anyone who does work for you emails their invoices to a unique email address. These are converted to bills for you to pay online only after you approve them. This keeps anyone from sneaking something in unexpectedly. Everything syncs to Quickbooks automatically. Nothing keeps your costs under control better.

It is often is the best tool for handling invoices as well. The reason is the network. Bill has millions of businesses signed up to electronically pay and receive money. Yes, you can use Quickbooks invoices too, but Bill does a much better job automating client payments. Using Bill, we have reduced our Days Sales Outstanding (DSO) to 18 days, and managing this is handled by a single team member and is not her full-time job!

CashFlowTool to guard your money

You can do this by spreadsheet, but if you have over 100 clients per month, things can get time-consuming. This little tool plugs into Quickbooks and does pretty darn good cash flow forecasting for up to six months in advance. It’s a new tool for us, but I am impressed, and it saves me a lot of time each week manually updating spreadsheets.

Divvy to control spending

Owned by, Divvy is a free company credit card and expense management system. As usual, it connects to Quickbooks easily. It allows you to create both real and virtual credit card numbers for employees to use. You can lock down how much budget they have, where they can use it including geographical + category restrictions, and notifies you for any out-of-cycle budget requests. This is MUCH better than giving employees company debit cards or requiring reimbursements via receipts (and yes, you get reward points too).

Gusto for payroll

Over the years, we’ve tried almost every payroll system out there. Nothing comes close to Gusto in terms of ease-of-use and customer support. Gusto also offers vacation requests and expense reimbursements.

Google Workspace for communications

There are really two easy choices here. We prefer Google over Microsoft 365. Google tools, in my opinion, offer superior collaboration tools with less training and maintenance for most businesses. Set up two-factor authentication, and you really have minimal chance of any security issues as well.

Zoom for video meetings

Google Meet is fine and Microsoft Teams is improving, but Zoom is far easier to work with on a daily basis if your company is in any way remote. From a client perspective, it is now universal as well. My advice is to ignore all of their other tools such as chat and phone unless you absolutely need it. In our experience, Zoom is worth the extra money we spend.

One suggestion is to take a few hours and get your branding in place. In our case, Zoom really is the front door of our business. We want it to look sharp. It helps us present well to larger agencies and companies.

MacBook Air laptops for low-maintenance computers

A MacBook Air with a two-year AppleCare warranty is bulletproof. If anything goes wrong, Apple fixes it. If you must work in the Microsoft world, then their Surface laptops with warranty run a close second. Most importantly, get everyone the same thing. There is a reason Southwest Airlines only fly 737’s – all parts are interchangeable, and everyone on the team can train everyone else. In my experience, a hodgepodge of computers has resulted in at least one or two people each month being out of commission for at least half a day. Running that math of lost productive time, you can easily get to $25,000 of lost revenue without blinking. Time is money. (By the way, if you have software developers, they usually have their own laptops, and as long as they support themselves and practice good security, my experience is to let them do their own thing).

Google Chat for quick team communications

It’s built into Google Workspace and Gmail. Super easy. No extra cost with something like Slack. Faster than texts. Built into Gmail. Has funny gifs. Teams love it.

Hive (or something) for project management

Project management tools are complicated. We chose Hive, but there are so many. I’ve heard great things about, Asana, Trello, etc. All work pretty much the same way. None of them work without being used consistently by everyone in the company and used – Every. Single. Day. A pretty common refrain around our business is, “Please put a Hive action in for me,” and it starts with our CEO. The absolute second you let up, it stops being used. As I said, we like Hive, but there are other options that work well too. (One additional piece of advice – avoid enterprise solutions like Atlassian Jira, where an engineer is needed to even turn it on.) This is a subject for a future standalone article.

Pipedrive for CRM

Again, there are many tools to choose from. After experimenting with a ton, Pipedrive is easy to use, has good sales pipeline management, and includes direct integration with Google Workspace with esignatures built in. As with project management, use it – Every. Single. Day. It has to start at the top down. Everything must absolutely begin and end here with sales. Another standalone article (or book) can be written here. As with project management, my experience is to avoid anything like built for enterprise clients.

Grammarly to make you look smart

It uses AI to fix grammar in everything you write. Do you think people don’t notice when you rush an email and mistakes go out? They do. Every email, proposal, and document you and your team write is a picture of your company. Put your best foot forward. As long as you fix everything underlined in red, Grammarly stops 95% of embarrassing mistakes. The free version works fine for most companies.

Loom to save everyone’s time

Nothing has improved our communications and decreased our time to close deals more than Loom. It is a simple plugin for your browser that lets you easily record your screen while also capturing your walking through it. Once you finish the recording, it instantly gives you a link you can send to anyone. We use it for sales proposals and to show each other what we are seeing for technical troubleshooting. It actually might be magic beans. The free version works for most, but the upgrade is cheap. Get it.

ChatGPT for getting started with AI

Oh, my, has this thing changed everything. Pay the $20 per month and get guaranteed access. We use it for everything from light marketing copy, SEO optimization to basic contract reviews – even debugging code. It’s so new that we are all learning AI together. Don’t wait. Dive in.

WPEngine for websites

We are different from many businesses in that our business IS a website. We use WordPress which runs on the WPEngine platform. It depends on your business, but you might be able to get away with something basic on Squarespace or Wix. But if you need to produce content, nothing beats WordPress, and WPEngine has the best customer service of any business I’ve ever seen. In terms support, we all want to grow up and be them. Some people say WordPress is not secure. I disagree as with WPEngine it is nearly bulletproof. Their security is top-notch which is critical when dealing with any website hosting. I would not recommend using anyone else for any reason.

Trainual for documentation

Trainual helps collect, organize, and communicate company standard operation procedure (SOP) documentation. For newer and smaller business, it is likely overkill and just adds an extra layer. If you have more than 10 employees, we’ve found that a Google Drive folder with SOP’s quickly gets out of date. Trainual also helps to onboard by offering progress checks, quizzes, and everything needed in one place.

Zapier for automation

Zapier is the glue that holds modern businesses together. In a nutshell, Zapier connects almost every online tool to every other online tool. For example, when we get a new client and enter it in Quickbooks, Zapier creates a customer folder in Google Drive, sends a notification to the team in Google Chat, and emails the client’s finance department a welcome email with our W9. Hundreds of different software packages can now talk to each other. It. Is. Amazing.

SurveyMonkey for NPS

There are probably thousands of survey tools out there. SurveyMonkey might be habit, but it has all we need, and most importantly, it has a licensed NPS tool. Net Promoter Score (NPS) is the best way to get client and team sentiment about how you doinging. Above all, it forces action with low scores. I may not know what is wrong, but I damn sure know something is wrong. And that means I’ll likely do something to figure out why and fix it.

Predictive Intelligence for team dynamics

Predictive Intelligence (PI) requires training, but offers a way to assist in both hiring and managing by helping people understand their natural behaviors. For example, I am introverted by nature and require time to recharge after “people-ing” a lot. Liza Graves, is an extrovert and gets her energy the more she engages. We now know this about each other and adjust our work and social lives accordingly. Other behavior patterns it helps to identify include attention to detail, patience, ability to collaborate, and even how fast people can learn new skills. PI helps people find their best roles and teams to communicate because they understand how each person fits into the plan. It’s not magic, but we’ve found it to be an amazing tool to foster diverse skillsets and backgrounds to work well together.

Objective Management Group for sales hiring

Despite having a laughable acronym, OMG is the most amazing tool for sales hiring I’ve ever experienced. OMG screens not only for ability, but also for the “grit” and determination to make a sale. It’s expensive and worth every penny. Using OMG assessments, we’ve quickly gone through over 200 applicants to find only five that make it to full interviews. These candidates have generally worked out well from both sales skills, “sticktoittiveness,” and team fit.

Arbinger for staying grounded

We experienced The Arbinger Institute via a two-day training seminar put on by EO Nashville. In summary, it flips traditional company culture-building training on its ear. In their experience, both personal and organizational success comes from a realistic and positive mindset. You can’t fake it, either. After our initial foray, we brought them in for our entire team. It was powerful and impactful. We now are looking at more affordable online options for new team members. If you want to explore more, I highly recommend reading Leadership and Self Deception.

The Biggest Warning

Sorry for the last story here, but there is a payoff…

After selling our first company, which had grown to about $10M in sales, we were purchased by a large public company. Several executives were having a really hard time understanding why anyone would want a software solution that didn’t target the biggest of the big companies (ours went after the mid-market). One, in particular, gave me a lot of hell about it, given his background of working for giant enterprise technology companies selling to other giant companies. When I left the public company, I figured we would never talk again.

Flash forward to about five years later and, lo and behold, I get a voicemail from him out of the blue. “I need your help.” When we finally caught up he told me his story. He’d left the big public company and moved to run operations for a firm selling solutions to community banks (which certainly fall into the SMB category). If memory serves correctly, this was his direct quote: “I’ve learned that you can’t put enterprise software in the dryer and expect it to shrink like a sweater to fit small companies.” They had spent a LOT of money on some fancy tools that flat-out didn’t work.

Together we put a plan together for them to build some data tools that were better suited for smaller clients and a lot less expensive. We are still friends to this day.

The moral of the story and the biggest warning I can leave you with: DO NOT BUY ENTERPRISE SOFTWARE AND EXPECT IT TO WORK FOR A SMALL BUSINESS.

You will hate it.

And, the expense can kill your business.

And the enterprise software vendor will hate you because you take up too much support time for too little revenue with no growth potential.

The Final Tool


Blueprint.Inc | StyleBlueprint

“You do not rise to the level of your goals, you fall to the level of your systems.”

James Clear

Strategic planning – What does that even mean?

The best ideas in the world aren’t anything without execution. Learn from others’ mistakes (in this case, my mistakes in particular). Once you eliminate the idiotic, sometimes you end up with a few pearls of wisdom.

Have a great mission, a basic financial model, and then follow a basic pattern that allows for agility and a fast tempo. Business plans are out of date days after you create them. Sometimes in hours. I get Eisenhower’s maxim entirely, “In preparing for battle, I have always found that plans are useless, but planning is indispensable.” With that said, the traditional business plan for a small business is, in my experience, counterproductive to a young company (and even some larger ones). Instead of rigid planning progress, hone your mission personally and with your team. Are you selling something that solves a problem for your customers? Do you believe in the value you deliver? Does a one-page P&L generate the profit you need to continue? Is there enough cash to get there?

Assuming yes, then start, and continue, the OODA Loop at a pace you need to succeed:

  1. Observe
    • Are your financials updated monthly? (Monthly Close Checklist)
    • Are your customers succeeding with and believe in you? (SurveyMonkey NPS)
    • Does your team know what to do and when to do it? (Trainual)
    • Are your competitors ahead of you? (Sales team chatter)
    • Ask hard questions.
  2. Orient
    • Bring the data together and get the most realistic picture of your world possible. (Regular meeting cadence)
    • Make goals as data-driven as possible. (Simple KPI’s)
    • Do not lie to yourself. If it’s bad, it’s bad. If it’s good, is it sustainable? Figure out what options you truly have.
    • Hope is NOT a strategy.
  3. Decide
    • Decide what to do next.
    • Make the decision quickly.
    • Do NOT kick the can.
    • Delaying a decision is a decision in itself and almost always not a good one.
  4. Act
    • There is a famous Special Ops phrase, “Slow is smooth. Smooth is fast.”
    • Work the plan you decided on.
    • Repeat this loop faster than your competition, and you’ll beat them.
    • It’s hard. It’s a grind. It’s the only recipe for success.

To the students of Col John Boyd, the originator of the OODA Loop, please accept my apologies. This is an overly simplistic view, and I’m still learning. I’ll actually be studying his work for the rest of my life.

Create a daily, weekly, monthly, quarterly, and annual reminder list

Put this in your project management system. We use Hive for this. In my experience, you won’t remember everything without recurring reminders. For example, I would do the cash flow forecast weekly for a while and then forget for a month. Bad mistake. Challenge your team to make a list of everything you need to remember. From sending W2s in January to watering the office plants weekly. If you can make it recurring, you are much more likely to get it done. Forgetting isn’t always a killer, but sometimes a forgotten 5-minute task of sending a client a report can result in a 5-hour meeting to talk them off a ledge.

Daily huddle – The most important meeting

What did I do yesterday? What am I doing today? What is my top priority for today that I am committing to getting done? Everyone goes around the room, and you never, ever get into the weeds. Pro tip: start with a random person each day and ask them to choose the next person. It forces everyone to pay attention. It works on Zoom or in person. It is the most critical ritual we’ve ever found for a successful organization. It takes leadership to start and leadership to continue. If you have to miss it, send in your notes ahead of the meeting. If there was one thing in this entire blueprint I’d recommend, it is to implement a daily huddle. It’s that important.

Weekly 1:1’s with Team Members

These are 15-30 minutes each week to check in. Most importantly, we use a template for questions asked each week. You can see ours here. Each team member should complete the 1:1 form each week before the meeting. Do this each week and you’ll never get too far out of alignment.

Quarterly planning retreats

We call our quarterly planning time our “(S).Inc Up” (we at are so funny). In the last three years, we’ve basically become a virtual company. These four retreats each year are a 100% requirement to be onsite no matter where you live. Zoom works well, but nothing replaces breaking bread with the team. We have two-day, two-night retreats, but we have also done one-night, one day when necessary. We do quarterly goal planning, team progress reviews, and always have lunch catered and dinner as a team. Here is an example of an agenda for the day we use.

Monthly team meetings and lunches

We do an hour meeting each month where we go through annual and quarterly goals progress. Each department manager gives a brief update, and then we go through the numbers including profit sharing. We have lunch at the office for our in-town team (as we’ve gone nearly virtual in a post-Covid world). If you’ve picked up on a theme, it is that communication takes way more time than you think. And it still probably isn’t enough.

Monthly Green-Yellow-Read Account Review Meeting

Seriously, my favorite meeting of the month. It takes 45 minutes, tops. The agenda is simple: the sales team and the ops team go through each client in alphabetical order and assign one of three ratings:

  • Green – Everything is going well
  • Yellow – I’m worried about our relationship with this client. It could be anything from “they aren’t responding to requests” to “the economy is hurting their business”
  • Red – This client is at risk. Doesn’t matter why, but something is definitely wrong and everyone needs to know

This is a quick judgment call. No overthinking allowed. After rating all clients, we go through the Reds and Yellows to develop an action plan.

We have 200 clients here, but even if you have 20, I think it would help. It has been amazing in keeping us aligned on our clients’ success.

Blueprint.Inc | StyleBlueprint

Annual management goal setting

A day to reevaluate the mission and to plan the major themes for the next year. From this must come a realistic sales projection for planning the budget and no more than three Key Performance Indicators (KPIs). Just three.

Blueprint.Inc | StyleBlueprint

Engineer profit

Based on the book, Profit First, flip the typical P&L upside down. Start with your realistic and attainable sales goal. Then figure out what real profit you must have to meet your personal objectives (that’s for you to figure out). Subtract your profit goal from your sales goal. Guess what? This is the number you’re allowed to spend on expenses. But wait? We need to hire more people! No, you don’t. We need more equipment! Not without the sales to support that investment. It makes life so simple. Businesses must make money! Without profit, there is no reinvestment for growth.

Sherry Deutschmann “Lunch with Lucy” Profit Sharing Bonus

Sherry has created the best bonus program we’ve ever seen from her book Lunch with Lucy. It’s very simple – after the financials are closed each month, take the Net Operating Income (profit before owner’s expenses) and multiply by 10%. From there, you have to pay taxes, which is easy to explain as your employees do, too. So subtract 33% for the government. That’s your bonus pool. Now here is the magic – everyone gets an even share. Period. Managers don’t get more. New people don’t get less. If the company wins, everyone wins in a way that is tangible and visible. Pay it immediately in a special bonus payroll run. Everyone is aligned for profit. You hire when you need to hire, and your team helps you find people who fit your culture. In months that don’t have a profit, it makes you a better leader and work harder to get back there. This is so much better than a “Christmas bonus.” I’ve tried nearly everything through the years. This just works.

Plan and Monitor Cash Flow

To paraphrase Donald Miller, if a business is an airplane, the cash is its fuel. Without cash, the best business ideas fail. It is wildly important to review your cashflow weekly and never, ever get caught off guard. We’ve been taught a method to do this by a spreadsheet which works well if you have a person with time to track everything down. We’ve recently found CashFlowTool (see above). We regularly review a very good six-month forecast that considers payroll, credit cards, and historical annual expenses. It’s another “close to magic” solution. Again, without planning cash flow and understanding the relationship between sales growth and how much you need, things can get very bad, very quickly, even when the P&L says things should be great.


Build checklists for all of your products and processes and then, whenever possible, build them into your project management system. I highly recommend the book The Checklist Manifesto. It’s one of the best business books I’ve ever read and explains why the human brain thinks it can work without them. Spoiler: the human brain cannot consistently work well without checklists.

Checklists are also the canary in the coal mine for your systems. Your business = your people + your systems. Without good systems, your good people will leave.

W. Edwards Deming recommended looking at the world in terms of “special” and “common” causes. If in your organization you have a small number of people making mistakes and performing poorly, it’s probably their fault. You should spend your time working with them, or transfer them to other jobs, or if neither of those options is feasible, remove them. If it’s more than 10%, though, then it’s the system’s fault and you should put your effort into fixing the system and quite blaming or exhorting the people in it.

Chet Richards – Certain to Win

Monthly close checklist

The most important checklist you have. In my experience, there is nothing more vital than thoroughly and completely closing the books each month. No later than the 15th of the following month and faster if possible. This lets you run the “Orient” step of your OODA loop with confidence. You know how your products are being accepted by your clients via new sales and possibly client churn rate, depending on your business. You know how your expenses are tracking. You know how cash is flowing. You know your tax liabilities. Miss just one month, and the errors start to pile up. Miss just one month, and people watching realize they might be able to get away with stealing from you. Never, ever, ever skip closing the books. Hire a bookkeeper if needed (and if you have ask, you 100% need a bookkeeper). It is worth the time and the expense.

Use APA to teach process the right way (keep reading to find out what APA is)

Everyone tells you to automate your workflow. That sounds great until it becomes absolutely overwhelming and you end up with paralysis by analysis. Or at least that is what happened to me.

Another way to proceed is find those tasks that are small but highly visible and important to the team. For example, we had issues with orders being incompletely entered into our CRM system. This lead to mistakes in production because all the information for execution wasn’t included in the job setup. There was no way to force this entry in Pipedrive.

Enter Zapier. With Zapier, we set it up to “listen” for new order entries. If information is missing, Zapier resets the order to “pending” and sends a message to our team Google Chat with a picture of Scooby Doo that says “Ruh Roh – order information missing!” This drives the sales team crazy but it has become somewhat of a fun joke that helps us focus on process improvement. We also make dramatically fewer mistakes these days.

My friend Mike gave me a name for this: APA (Automated Proper Assholery). I love it!

Start small and keep going. New automation opportunities will present themselves…

Johnny Decimal – Organize Everything

This is our newest find: Johnny Decimal. It’s so simple, I can’t believe we haven’t all been taught this method to control folder spam. I’ve done it 1,000 times: Jeez, I am not sure where to put this so I’ll just create this folder here…

Then I have no clue where I put it. And search can’t find it because I named it something weird. Dammit.

What is even more amazing is that it is kinda fun. At our last quarterly planning retreat, we spent over an hour creating our working structure and everyone got into it:

Blueprint.Inc | StyleBlueprint

The result was the following top-level structure:

Blueprint.Inc | StyleBlueprint

It is so simple that it is kinda dumb. But wow, you know where things go, and while it can’t stop everything crazy, it has helped a lot to talk about how to keep track of digital chaos. We still have much to learn to do Johnny Decimal well but the start has been great.

Naming conventions will be for another day…

Corporate Documents Folder

When we sold our first business, I learned one very hard lesson from two words: Due Diligence. I had no idea what this meant, and we were woefully unprepared. The buyer asked for everything. Not only did we not have everything, but in many cases, we didn’t have anything – including valid contracts for several of our largest clients (they had expired). I couldn’t even begin to guess where the articles of incorporation were, either. So in a 72-hour, caffeine-fueled bender, we got reams of documents together and dragged ourselves over the finish line. It was a terrible experience, and I vowed never to let this happen again. So the next time we took our medicine early. We hired a former investment banker to run pre-due diligence on ourselves. We found everything and organized it into a set of folders that would bring a smile to the face of any M&A lawyer. It was all there and the process, while still terrible, went much better the second time. What I learned was this – after you get revenue going and profit in place, immediately take the step of organizing your company documents like you were going to sell even if you aren’t. Banks need it. Mortgage bankers need it (especially if you are getting paid with a K-1). Insurance companies need it. Basically, every time you have to stop to find a document you are burning time that could be used for sales, marketing, or sleep. Here is a picture of what our folder structure looks like:

Blueprint.Inc | StyleBlueprint

Steal it and take a week to create a closely-held but shared drive with everything you need handy. It is worth the time.


Turn on 2-factor authentication for Google Workspace and any program that handles your money like Quickbooks or (they pretty much all require it now anyway). Get MacBooks and make sure encryption is turned on. Tell your bank that you want any wire transfer confirmed via a phone call. Then unless you are in a highly regulated industry don’t worry about it. Seriously, do these few things and you are ahead of 98% of companies out there. Bad guys will move to easier targets.

Have banks statements and tax docs mailed to your house (or your email)

Not to sound like a cheese country music song, I am convinced that most people are good. With that said, the ones that aren’t all the way good will be good if they know they will get caught.

Years ago, a keynote speaker at a conference I attended was a “forensic small business accountant.” No one wanted to go. This little nerdy guy came out, sat down on a stool, and started to talk. Ten minutes into his presentation and we were on the edge of seats. He said, “It’s always the office manager or bookkeeper who steals from you.” He then proceeded to tell us why. Most SMB’s lack the controls and separations of duties to prevent internal fraud. Eventually, people who take advantage of situations, for whatever reason, can find these gaps and exploit them.

“Good fences make good neighbors,” as the old western saying goes. Make it clear to your team that you regularly review the books independently. Use tools like DivvyCard so that employee expenses are monitored (and they don’t have to keep track of receipts which is a plus for everyone). Require double signoff on all payroll runs. Call your banker and require they verbally confirm any transactions and confirm via email – then if they don’t the bank will be on the hook (they might try to wiggle out of it but it will be harder). Close the books every month and review them. Ask questions publicly. Your team now knows you are on top of things which is good in many ways.

We can speak from experience here. Many years ago, our previous COO neglected to pay the payroll taxes for almost a year. Since it was her responsibility to check the PO Box, she also hid the dozen+ overdue tax notices at her home until it was too late. Not classic fraud, but it certainly extended her own payroll longer than it should have been as we thought the company was doing better than it was.

Have a laptop program

There is a reason Southwest Airlines flies only 737’s. All pilots can fly any of the planes as they are all the same model. Any mechanic can work on any plane. Any flight attendant is certified on any plane. Any spare part can work on any plane. Why would laptops be any different? High-quality, standard equipment pays for itself quickly when you factor in any downtime.

Our policy is simple. We will buy a new team member a new Apple MacBook Air. If they stay for two years, then it is theirs to keep. If they leave before then, it must be returned. We put it all in writing, and everyone signs off upfront. Here is an example.

These computers aren’t that expensive and the only downtime we’ve had by anyone in the last two years were older, refurbished computers that pre-dated the policy.

The one exception we make is for developers. They want their own stuff, but the good news is they also like to do their own troubleshooting. Let ’em have at it.

Get a lockbox if you get a lot of checks

Most banks offer a lockbox service – your clients mail checks to a PO Box that the bank checks every day. They immediately deposit the checks and send you a digital image to record in your accounting program. Service probably costs about $200.

It. Is. Totally. Worth. It.

I know $2,400 per year is a lot of money. It even took us about a year to slowly get our clients to change their address for us (we mailed the postcards repeatedly to get it done). Now we never miss a check, and there is never a delay in getting it in the bank. It probably saves 1-2 hours per week and reduces our DSO by 2-3 days. Cashflow is everything. This more than pays for itself and is one less chance for issues with client payments.

Coaching and learning resources we’ve used and recommend

No one would try to excel in a team sport without a coach. Why would business be different? We could do an entire post about this, but here is a quick summary of some coaches we’ve used that have helped our business.

Find an organization that can offer support and learning opportunities

One of the most valuable exercises I personally experienced in business is to find a group of peers to share business experiences with. It is common to fall into the trap of thinking it is “me vs. the world.” In reality, without a good mentor or a group to safely bounce ideas off of then you likely will lose perspective and head off in a crazy direction. When flying, pilots who get “spacial disorientation” usually crash their airplane. Business is not different.

While there are a lot of good groups out there, this is my pitch for EO (Entrepreneurs Organization). If you have over $1M in sales, EO provides amazing learning opportunities and non-competitive, totally confidential small group peer “Forums” for experience sharing.

If you haven’t reached $1M yet, most EO chapters have accelerator programs for business fundamentals.

We are members of the Nashville EO Chapter which is one of the largest in the United States. However, EO is a global organization and there are chapters around the world. Check them out. And if not EO, my strongest suggestion is to find something where you can learn and contribute. It is an amazing “check valve” for entrepreneurial stress.

On Marketing

There are so many things to go over that I won’t even attempt to try in this already too-long article. This will be a story for another day. However, it is important to be organized in your marketing efforts and that starts with an inventory of all your marketing channels. Make sure your company pages are set up and look “good enough” (not perfect) for:

All of the pages are signals to search engines that your business is real and worth of being found.

Things that Don’t Matter

Things that don’t matter – at least until you are bigger and usually not ever:

Your domain name – What matters is Google. Write good things and be around long enough for people to find you. Then when people search for your name it pops up in the top of the search regardless of what you paid for the domain name.

Your logo – Just be professional to start. Just have something decent and put it on all your emails and communications. Nothing is worse than a plain document with no formatting or logos. Well, a plain document with typos is worse, but that is (mostly) solved with the previously mentioned Grammarly.

In most cases, your office space quality – Jeez, in 2023, the debate is whether or not to even have office space. If you are retail, different story, but for service businesses, just have something clean with windows. Overspending on long leases is a sure fire way to run out of cash.


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“As far as I am concerned, the problem is me”

I learned this from the book Leadership and Self Deception by the Arbinger Institute. But I really learned this by making mistakes over thirty years and trying to find ways to prove it really wasn’t my fault. Except it was. The team keeps making the same mistakes over and over? My fault for lack of checklists and poor communication. A toxic team member disrupts the business? I never should have hired them or let them stay so long.

It’s hard to think this way. Radical accountability isn’t taught; it’s learned the hard way if you are lucky. For me, it meant sleepless nights riddled with self-doubt after I finally saw the light and realized the time I’d wasted. But it becomes a beautiful feeling when you see it finally work because you end up helping everyone around you. The world slows down a bit. Slow is smooth. Smooth is fast. Give it a try.

“Cynicism is cowardice.”

General James Mattis wrote this in 2019 and I just ran across the quote. It hit me hard because I spent much of my early career completely guilty of looking at business, and life, too cynically. “They’ll always act this way” or “We’ll never compete against the big guys.” With that attitude, it became a self-fulflilling prophesy.

I certainly don’t recommend running around with a Pollyanna attitude that everything is peachy keen and karma takes care of all slights (the world is tough and many times good things do happen to bad people and bad things do happen to good people). However, the belief that the universe is stacked against us is just flat out untrue. The universe doesn’t care one way or another. Work hard, and get a bit of good luck, and good things will happen. Not always, but many times. People may not treat me well, but I can control how I treat people. Most people, as the sappy country music song goes, are good. And even the ones who aren’t good have a story.

The second part of the quote is good as well, “And cynicism is corrosive when it saturates a society, as it has saturated too much of ours.” But this is a story for broader context on another day …

10,000 hours is really 20 years

“Wait, your math is wrong!” Assuming a 60-hour work week (as a business owner) then 10,000 hours is a little over three years. “So, I am going to work so hard that I’ll have my 10,000 of business experience to be an expert.” Nope. You might work ten hours a day, but you’ll be lucky to get two hours of practical business experience in the real world – so maybe 10 hours a week. The rest is fire fighting and doing work.

So it takes 20 years to finally get your feet underneath you. At least if you are stubborn like me. Having a mentor helps. Having a learning spirit helps. I know people who picked it up way faster and as a result found success earlier. It is possible to skip steps, but my experience shows that it requires humility (which will always be a struggle for me) and deeply observing the world (which is hard for those of us with low patience). But then again, I also know people who haven’t even started trying at all. Guess where they are?

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Don’t feel bad when it all seems crazy. Start. Absorb. Embrace the suck. You’ll get through it by trying and sticking to it. Above all, laugh when you can. “You bought the ticket. Now take the ride.” – Hunter S. Thompson

On business partnerships

When you go into business with someone, and equity is involved, it is one of the most potentially rewarding and dangerous decisions you can ever make. Bar none. And never, ever, ever do a 50/50 partnership.

In my first business, I was incredibly lucky. Not only did I have a great business partner, it was 50/50. With this success, I naturally thought this was “normal.” Wow, was I wrong. And lucky. After a decade we sold to a public company and remain close friends.

The second go-around wasn’t the same. We ended up with seven equity partners (bad idea). No one person had managerial control (bad idea). It was a terrible mistake for everyone involved. When we realized that we disagreed on the company’s direction, it devolved into an ugly standoff. We eventually sold the company and went our separate ways. I will never talk to three of those partners again. The feeling is most assuredly mutual.

In the last few years, I’ve talked to hundreds of entrepreneurs. Stories of terrible business partner relationships are rampant. Businesses without strong operating agreements with safe ways of handling disputes seem to end poorly. Friendships are gone – usually permanently. Lawyers get involved and they make a LOT of money resolving the issues. Your money.

Start with the assumption that things can and will go wrong and that someone must always be in charge. Not an autocrat, but someone who can break a stalemate when the time comes. And it will come. Every situation is different, but insist that there are protections in the Operating Agreement and sit down beforehand and walk through them. If you don’t agree then, don’t go into business together.

If you end up in the situation I got myself into, don’t kick the can. It may seem crazy at the time, but either get things fixed now or consider a breakup. Your mileage my vary, but the short term pain will save years off your life. Someone once told me, “you get like five deals in a life” which is pretty scary. Don’t waste one to two like I did.

On the Sacristy of Compensation

Never joke about or screw with people’s comp. Never allow anyone to joke about comp, either. Never, ever miss a payroll. If there is a delay, treat it as a pure emergency and offer to cover anyone’s late fees. This one’s simple.

Hire for your values

Everyone is going to tell you the kinds of people you need to hire. Or, as an employee, the kinds of companies you need to work for. Create an organization that works for your values. Want to work all the time? Make sure your team has workaholics. Correspondingly, enjoy your time off? Don’t hire a bunch of workaholics. We all know who we work well with. Don’t go with the all the advice you hear from the gurus – you know.

Prescreen your candidates

We’ve learned that you can learn a lot about candidates by asking quick questions ahead of time before an interview. Here is a sample one one we use. The most important question is to have an upfront conversation about salary expectations. It is amazing just how far off both parties can be. It’s also amazing how the best candidates have done their research and know what the market is paying (and are good at negotiating a deal that works for everyone).

Interview questions and references

Four interview questions to always ask:

  • What do you like to do?
  • What do you not like to do?
  • What will your references say when we call them? (and always call them)
  • What does your job and salary look like here for you in five years?

These questions will get to the heart of cultural fit. When done with the interview, always, always, always call the references. You can read more in Who: The A Method for Hiring.


When my first company was purchased by a large public company, I learned a very valuable lesson. We had some great young developers that were rapidly leveling up skills-wise. When annual reviews came around, I was told we could offer the really great ones a 3% raise. I calmly explained that every one of them could leave now for 15%-25% raises. Sorry, 3% is the best they could do. All the developers left.

There is a term in finance called “mark-to-market,” which means that the price of an “asset” on the books is adjusted to the real-world value of what someone would pay. People aren’t assets, but offering a great young employee a 3% raise when the market clearly will pay more is basically saying they are objects. In my experience, you don’t have to match every offer or bend to the whims of the market as long as you pay fairly and provide a great place to work.

There are plenty of stats out there about how the cost of hiring a new employee is something like 3x the cost of keeping one already on your team. Having an ear to the ground and paying people a fair market salary is a lot less expensive than recruiting. If you offer a great place to work and pay in a reasonable range, most people won’t be looking to leave.

Write everything down – memory is almost always wrong

When you get a moment, I highly suggest this Malcolm Gladwell podcast episode: Free Brian Willams. It is all about memory. In particular, it is all about how bad our memory is as humans. It completely changed my view of how to deal with people in high stress environments – which includes lots of days in business.

I’ve dealt with people with bad memory. It’s hard from someone to back down once they’ve called you a liar – even when you show them proof it was the other way around. My experience shows that a better way is to always be taking notes and then share those notes. Good notes helps everyone’s memory – especially people with poor memory that call people liars. Good notes prevent a whole lotta fights.

Never, ever, ever get mad (well, at least not more than once per year)

Almost every time I’ve gotten mad in business I’ve regretted it. Staying calm is a superpower that I wish came naturally to me. Calm people make calm decisions. Slow is smooth. Smooth is fast.

With that said, sometimes getting mad is just showing emotion. Teams need to see you care about them and the business. And sometimes that means getting your hackles up. But seriously, when it happens frequently, I’ve found it is me not them.

Don’t worry about getting even

Respond to every online employer review calmly. Don’t let that scummy competitor that you just know cheated make you say things you can’t 100% prove. Feel free to add to this list of what not to do. I’ve got plenty more examples of dumb things I’ve done with revenge on my mind.

Focus on your team and your clients. It would be great to say karma will handle everything else. It probably won’t. Buy your success will.

“The best revenge is massive success” – Frank Sinatra

My Favorite Twitter Accounts

Say whatever you want about Twitter; some amazing business and life resources are on the platform. If you can avoid the “buy my course and get rich hucksters,” then here are a few good accounts to follow and read:

Feel free to suggest more good ones! And anything else. My goal is the keep this updated and add new great things we learn along the way. My email is jay.graves@blueprint-inc or you can use the blue “Feedback” button on the right.

Thanks for reading!

Revision History

  • 1.0 – June 5, 2023 – Initial version
  • 1.1 – June 19, 2023 – Added enterprise software warning
  • 1.2 – July 9, 2023 – Updated for grammar, clarity, and a few missing images
  • 1.3 – September 25, 2023 – Added Johnny Decimal
Jay Graves

Jay is Chief Operating Officer at Blueprint.Inc ( based in Nashville, TN (better known as the home of He manages financial, technical, and process management, supporting small business clients around the South. He has over 20 years of experience in technology management, software development, strategic business development, and bootstrapped startup companies.