Module 7 of 9
In Progress

Delegate or Suffocate

Not sure about you, but coffee has always helped me focus. Being ADHD and sometimes being completely stuck by the sheer amount of thoughts I have at any given moment. In the fall of 2017, on a brisk Monday morning, I needed coffee a little bit more than usual. I was in one of my first offices – I mean coffee shops – and I was swamped, exhausted, and doing way too much. I had 25 designs to finish for a client. 25?! I wasn’t going to even get close to finishing this project without help. But, I didn’t have enough money for help. I priced the project just right, just enough margin to be profitable, but not enough to sticker shock the client. 

Crush it, sleep is for the weak, hustle harder, be a lion! All the entrepreneurs I’d followed on Instagram were shouting at me in my imagination. I needed sleep. This wasn’t a one-time thing either, this was my life. Too much work, too little time, and 50% of my profits going to hipster coffee shops whose coffee all tasted the exact same. I was trading all my time for money, my money for coffee, and thus was the endless cycle of a coffee shop entrepreneur. 

I became an entrepreneur to buy back my time! What a scam! I spent years going in circles, like most entrepreneurs do, trying to find a balance. Thinking I didn’t have enough money to afford help. I can barely pay myself! Pay yourself first right?!

If this resonates at all with you, at any point in your business, this module is for you. Whether you’ve started hiring already or it’s just you sitting at your kitchen table or the table at a coffee shop that they made way too small for most reasonably sized laptops.  

Finally, whether it was audacity or the coffee talking I realized something. I had money, sure it was for bills and whatnot, but I had money whatever it was for. I could trade my time for $50/hr, and spend 2 hours doing the work OR I could use half the $50/hr to pay someone else $25/hr to do the work, keep $25 an hour, and buy back my time at $50/hr by going out and selling $75/hr instead of eating the hour working. This struck me like a ton of bricks. 

That was a mouth full, sorry about that. Let’s break that down a bit though because I feel like it’s one of the most misunderstood concepts when entrepreneurs first start in business. Well, I’ve even seen seasoned business people miss it. 

You’ve probably been told that money is the most valuable thing in the world. But it’s not, mental capacity is. But time is the second most valuable thing. Time is the only thing that creates. The richest people in the world got there by buying other people’s time, not by doing all the work themselves. Your hour is more valuable than the $50 product, but since you’re building the $50 product in an hour, it’s only worth $50. When you’re NOT building the $50 product and instead pitching customers new and exciting products the value of your time is linked to how much value you can create for a customer, not how much time you spend doing what you do for the customer.

When you focus on adding value and sales instead of always doing the work you buy enough time to sell double the customers you were selling before when your time was focused on doing. 

For example, when I was designing logos, I charged $250 in the beginning. It took me about 4 hours, which was about $62.50 an hour. Not bad right? Wrong, horrible! I had a LOT of experience building logos and brand design. When I paid someone to do it for me and gave them half, or $30/hr, I was able to offer my client my expertise, not just my time, and give them brand advice, marketing ideas, and even throw in a website audit. This all added more value and justified a $500 logo package. Between myself and my designers, time was more like $100 an hour, and $70/hr profit instead of the $32.50/hr profit. 

I was also freed up to sell double the business I sold before because I had more time to build valuable relationships and cultivate referrals. This is how I scaled all of my companies; by slowly and meticulously trading my money for someone else’s time, so I could go make more money, and trade that money for more time. My agency is now a team of 45 and there’s no way we could have gotten to $3 Million a year without scaling the team. 

The first fear I had when hiring was “what if they’re not as good as me?” and then of course “what if they clock more hours than I can pay?”

Firstly, if someone can do a job 50% as good as you, hire them. If you’re going to take the leap from entrepreneur to a business owner you’ll need to learn to duplicate yourself in your employees. If you can’t take someone half as good as you and help them be better, you shouldn’t hire. 

Eventually, the goal is to hire people far better than you as that’s the only way you grow as a leader and as a company. You’re simply not the best at everything. I automated my business by hiring someone that was 10x better at managing it than I was. But the budget doesn’t always allow that, especially in the very beginning. 

Secondly, if they save you even half your time, the value isn’t that you just “get your time back” the value is you get to go sell more business and actually build a business, not just a service, with that time. Your focus should be on how to continually add more value to your customers so you can raise prices, optimize operations, and grow a business. This short sacrifice of profit or even revenue pays off exponentially over time. 

After running myself into the ground with the “grind” I finally let up and hired my first employee; who still works for me to this day, by the way. Training her took some time as I’d never tried to duplicate myself before, but afterward, I realized how much time I truly wasted being a workhorse and not actually building my company. I was just a W2 employee disguised as “controlling my destiny.” 

I have a friend who started in the exact same spot in business. We both started web design companies, both of us took similar clients, both used the same tools, you get the idea. Today I run a $3M/yr agency with 45 employees that started as my solopreneur web design company. Today, my friend is still building websites for companies by himself. 

The only major difference between us was that I hired when I didn’t have the money to. I urged him to do the same, but the response was always “I don’t have the money to hire anyone.”

There’s more to delegating though than just making more money. It’s about being a better business person and leader. A good leader focuses on what they’re really good at and delegates the rest. 

I know this is easier said than done. I’m not deaf to the struggle at the beginning of a business when money is the last resource you have. That’s why I wrote this module, to help you decide…

  • When to hire
  • How to hire 
  • Who to hire
  • When to fire 


Tread lightly into hiring as you’re assuming a leadership responsibility that a lot of people don’t take seriously. People matter more than you making money and that should reflect in how you hire, lead and let go of your staff. The best leaders see potential and help call out passion and purpose in their staff but understand the weight of helping provide for families and people’s well-being. 

Being someone’s boss is about serving them more than it is about them serving you. Serving an employee looks like enabling someone to become the best version of themselves while working at your organization. Empower people and do more for them than they do for you, and no just paying them does not qualify as justification to not add to their lives like they’re adding to yours.

Lead people out of a place of experience; where you’re not asking of someone what you haven’t first proven possible. Hold accountability on yourself and your employees, this will create mutual respect and understanding. Lastly, lead from a place of candor and honesty in your business to create an open environment where people feel safe to bring up issues and don’t just bury them until the day they quit. 

Hiring someone is a heavy responsibility and commitment to help them succeed just as much as they’re helping you succeed. 


When to hire?

In the beginning, it doesn’t always make sense to hire an actual employee. Instead outsourcing to another contractor can present a perfect in-between solution. This allows you to pay someone on an hourly basis with no commitment to an allotted amount of time if your revenue or workload can’t sustain full-time work. 

But when should you even start thinking about hiring or outsourcing work?

My simple rule is that the best time to hire a contractor is when 30% or more of your time is spent doing something you don’t enjoy doing or more than 75% of your time is spent working instead of building – I’ll define “building” in a bit.

When you’re spending 30% of your time doing something you hate doing, ie. spreadsheets, books, etc, etc, you’re actually eating momentum and mental capacity from the other 70% of the time, making you less efficient and less effective business person. 

Generally in the first year or so of building, the ideal breakdown of time is 50% doing what you love and 50% building. Over time this ratio changes dramatically depending on where you’re actually trying to go. 

If you’re needing anything under part-time work, I recommend outsourcing to a contractor that is doing something similar to you (this ensures a cultural alignment as well) and finding someone that is interested in potentially going full time in the future. 

If you’re swamped with work (maybe 80-85% of your time working on deliverables) and can’t find time to talk to customers or take potential new business meetings then it may be time to consider actually hiring someone on staff (don’t worry they can still be a 1099 employee which adds more flexibility.) Depending on the amount of work you have, you can save a lot by giving someone a salary instead of paying hourly, this is because a lot of people would rather a guaranteed amount than a fluctuating amount monthly. 

These numbers are completely arbitrary and different for every person and in fact, every business. But It’s my personal rule of thumb when starting a company. 


Non Service Industries 

If you’re not in a service industry and instead of building a product like a SAAS (software as a service) or something similar, hiring could look very different. Often when building a product instead of a service it looks more like hiring out of the gate unless you know how to build every piece of the product. 

When I built the app software for churches, I didn’t actually build the software. I knew nothing about development, so clearly I couldn’t wait until my workload was 80%. Instead, I had an idea and I went online to find developers that would do the work within my budget. 

I did on the other hand know how to market and sell a product, so I focused on getting customers and selling in the beginning. Eventually, I needed to hire a salesperson to take my role and a customer service person to handle questions and issues. 

No matter what business you’re in, outsource what you’re not good at or hate doing, focus on what you’re good at and love to do, delegate and duplicate yourself as you grow. There comes a time when you don’t get to do what you love anymore because your employees are all doing the groundwork, so enjoy it while you can. I still dabble in design projects occasionally, because I love it, but there’s no reason for me to be doing it. 


How To Hire?

The first thing you need to do when hiring is defined the role and responsibilities. This may sound like an “on-the-job” lesson. But if you don’t start with specific expectations it will bite you in the ass later. So list out all the things you want the person to do and what the hourly and time commitment looks like. 

Next, post a job somewhere online. If you’re looking to outsource, the best place to find someone with similar skills is online via one of the following resources: 

  • UpWork.com ← This site offers high-end contractors but is a little on the pricey side.
  • Freelancer.com ← This site mostly offers developers and dev teams. I found my first few developers from Freelancer, they’re still on staff today working full time actually. 
  • Fiverr.com ← Fiverr is a common website for a small one-off tasks, sometimes you can find someone that is willing to fulfill part of your deliverable over and over again. 
  • Markethire.com ← This site is relatively new but offers awesome marketing contractors. 

If you’re looking to find a part-time or full-time employee (w2 or 1099) then the sites we use are Indeed and ZipRecruiter. Both offer great tools, Indeed is pretty pricey though. 


Who To Hire 

To be honest I’ve looked at maybe 2 or 3 resumes in the last 10 years of business and hundreds of interviews. A resume tells you where someone’s been, not where they’re at or where they’re going. Not to mention they can be faked. In the agency, when we started hiring we just needed someone to fill a seat. As we grew we realized the damage that caused and wished we would have paid attention to these 3 major factors when hiring: personality, culture, passion.

One of my friends (we’ll talk about this later) needed a job a while back and I gladly gave her one because I knew she was a great designer. As we grew we needed more designers and eventually hired her boyfriend as a de facto member, without going through any formal hiring process. Less than six months later her boyfriend had stolen $13,000 from a customer’s card, caused countless team culture issues, and ended up dropping more than 4 major projects the day he chose to just leave. When we had first started working with him, I had a strong feeling that he wouldn’t fit our culture and what he was doing wasn’t really his passion. I should have listened to that instinct. When I veered away from hiring off personality, culture, and passion I paid a price. 




By personality, I don’t mean the enneagram. I mean what they’re instinctively good at and enjoy doing vs what they hate. The type of person they work best with and the type of person that makes them want to pull their hair out. 

We have every applicant take the DISC test when applying for any position. This tells us almost immediately if they’re the right fit for the role, without even looking at their resume. Their resume tells you what they’ve done in the past, but statistically, over 81% of adults in America aren’t doing what they love. When you don’t do what you love, you do a terrible job.

The DISC is broken up into 4 scales: Dominance, Influence, Steadiness, and Conscientiousness. Most results are presented in the main trait and a secondary, such as DI, or Dominant and Influential. Results usually look something like this: 

But people are usually a mix of multiple personality types and the DISC is no different. The scale shows how dominant, influential, steady, or compliant you really are. When you learn to read the DISC you begin to learn why certain personalities are way better at things than others. For example, leaders tend to be high D’s. Politicians tend to be high I’s. But by looking at the level of someone’s S, even if it’s not part of their major 2 profiles, you can tell how steady that person will be over time. 

Here’s a quick breakdown of the DISC and their specific behaviors:

On the surface, you can tell if someone will be good at a job based on their major 2 DISC levels, but you can tell someone’s abilities by looking at the full picture. 

A low C level indicates they hate details, and thus will not be great and certainly not enjoy a job bookkeeping or managing as they’ll let a lot of details slip through the cracks.  

A low S level indicates they’re rather sporadic and hate doing the same thing over and over again so they’d do a pretty inconsistent job in data entry.

A low I level shows a low social capability, usually, introverts have low I’s. A low “I” would make a pretty bad customer service agent.

A low D level indicates a lack of dominance and leadership skills. A manager with a low D personality would botch the job because they wouldn’t keep any sort of accountability. 

You can do extensive research on the DISC profile, but even on the surface, the value of testing is irreplaceable. Using the DISC changed my understanding of my employees and created a more efficient organization because I didn’t just hire people because I liked them and they said they fit the role, I hired because at someone’s core they were good at and loved that type of work.

You don’t have to pay a fortune either, there’s a simple free DISC test we use to gauge the general range of the different levels: https://www.123test.com/disc-personality-test/

For incredibly important roles, ie. managers and directors you can use https://www.corexcel.com/ which costs around $100 for a test.



The second thing I consider before hiring is whether they fit the culture of the company or not. This might sound whisky washy but remember the boyfriend of my friend that I hired? They were about as far from the culture of the company as you could find. Politically, religiously, morally, even his work ethic showed the disconnect. 

Don’t get me wrong, you will always have and it’s fantastic to hire people of different beliefs as you, that’s what makes a diverse and creative organization. But there are core values that you and your company hold that when your employees deviate from, your organization suffers quality and a family environment. 

Any successful organization requires a common set of values. At the nonprofit app company, we all had completely different political beliefs, even some with different religious beliefs, but the common thread was our values: we loved what we did, we were passionate about impacting the world, we loved helping nonprofit organizations. 

Culture is what you allow to happen in your organization. Do you allow creativity? The freedom to make mistakes? 

Once upon a time, I had a sales team lead who after hiring I became pretty close friends with. He was a dynamic and persuasive person which made him a fantastic salesperson. Over time I began letting things slip through the cracks. Small things at first, like he forgot to record a demo (which was a team requirement.) but over time it became bigger, he got his commission whether he reached his goals or not. He would regularly talk bad about the product to other sales team members. 

This went on without accountability for about 3 months because I was allowing small things to add up to big things. Eventually, it cost me, multiple members of the sales team, because he had created so much lack of responsibility. The entire team was watching him and how I allowed things to slip. Soon, no one reached goals and got confused when we tried enforcing the pay structure. 

It’s important to not just hire, but reinforce culture over and over again. As a leader, this is one of the most important roles you’ll play in your organization. 



What is the prospective hire passionate about? Does their work show this? 

Sometimes this is easier to tell than others, ie. a designer’s passion is apparent in their work, so is a developer. A manager’s passion is a little harder to tell as they can’t supply a “portfolio” of the people they’ve managed and how they’ve made them better. 

You can usually tell after talking to someone whether they love what they do or if it’s a job. But if you can’t you can always design questions to figure out what’s truly rewarding to that person. People are passionate about what they feel fulfilled by or rewarded by. 

Here are a few interview question ideas to extract passion from roles without portfolios: 


“What about [role] excites you” 

“Tell me about a time you felt truly happy doing [role].”

“If you could do anything for free, and not worry about money, what would you do?”


Hiring friends.

The #1 question on hiring is “can I hire a friend?” 

I’ve hired a LOT of friends. Some worked out great and some didn’t…the biggest difference between a friend and an employee is expectations. Friends think you’re their buddy and they can get away with anything or won’t be held accountable. Employees understand you sign their paycheck. There’s a solid expectation of pay/result. 

The best answer I have is if you hire a friend, you can’t be their boss, put them under someone else. Secondly, friends make terrible employees but great business partners! The expectations of an employee and a business partner are vastly different and I’ve found it makes the world of difference. 

But truly this is arbitrary too and is more about you and that friend and your ability to be objective and lead them in the right direction and keep accountability. 


When to fire. 

If the earlier example of the sales team lead doesn’t scream “fire him!” I’m not sure what does. 

Firing is hard though, it sucks. Especially if you’re a high I or S on the DISC. Because you care about people and their families and often you become friends with the people you work with. 

The best way to fire is through expectations. When you first onboard someone, you have to be clear about expectations and responsibilities and even make them sign an expectations document. Allow 3 major screw-ups before you take action. 

I will always veer on the side of giving another chance, often to a fault. But when I have a signed document outlining exactly what I expect of someone and what they agree to do, there’s a little argument if they’re consistently not living up to it. 

Remember, people have families, and they matter. But you have a fiduciary duty to your company. By not letting people go, you can affect the rest of your organization, and performance in completely unconnected departments can suffer. 

Accountability is paramount to running a successful and well-oiled operation as you grow. I’ll be digging into accountability in the next module.