INSIGHTS | November 27, 2020

10 “Musts” For Start Up Companies

Lessons learned starting a company. I write about fun things, and other times I write about super-nerdy and technical things. Today, I thought it would be valuable to create a quick list of “musts” (at least IMHO) for anyone that has that crazy/ nagging idea that keeps them up at night. Otherwise, known as the […]

Lessons learned starting a company.

I write about fun things, and other times I write about super-nerdy and technical things. Today, I thought it would be valuable to create a quick list of “musts” (at least IMHO) for anyone that has that crazy/ nagging idea that keeps them up at night. Otherwise, known as the thought of starting their own company.

So let’s get on with it…

1) You’ll never be your own boss in your start up company.

Somewhat typical scenario on a Saturday evening…

Me: [Pours another glass of red]
Person: “So what kind of stuff do you do for work?”
Me: “Oh, I run a digital agency in Ravenswood.” (that’s a northside neighborhood in Chicago for y’all not living in Chicago…)
Person: “OMG, like totes OMG, you’re so lucky to be your own boss!”
Me: [Pours another glass of red]

The above scenario happens on a weekly basis (including the wine part), and couldn’t be further from the truth.

Every client is your boss. Not just the hiring person – but literally every single person on the client team.

It’s not a bad thing, it’s just the truth. If you’re dealing with a project that has 30 people from the client side – then you have 30 bosses. Combine that across a couple hundred projects – and it can be slightly intimidating. Every client, every point of interaction from the people that you’re building things for – they’re your boss.

Being your own boss is fictitious.

The local, independent coffeeshop owner has her patrons.
An up and coming niche author has her readers.
Bill Gates had his Board.
The President has his constituents.

Regardless if you’re on a local or national stage – nobody is their own boss. Ever.

2) Know your startup company more than anything else in life.

This may seem obvious, but there are a lot of people with a strong love and affinity for something amazing. Someone may love dogs, so opening a doggie day care may seem (and may be!) an amazing idea. However, a passion for something only goes so far. Has that person worked at a doggie day care? Do they know the demand in that area? How many people in that area are Googling for doggie day care services? What’s the profit margins for every single product in that store? What’s the employee turnover in that sector? What kind of insurance is required? The list could go on and on.

It comes down to one thing: understanding the minutiae of everything. There’s a point where you can hire smarter people than you to take on certain tasks, but on Day One – you need to be prepared for everything.

3) Be really, really resourceful.

Understand what you’re great at and do it yourself.
Understand what you’re good at, and learn to be great at it.
Understand what you’re really terrible at, and find the most economical way to make it happen.

The lowest rated skill as of this posting is the ability to be resourceful.

With a plethora of online learning tools ( is a fantastic one!), it’s much easier to learn new skills and fill in any gaps.

When thinking of starting a company, if you have more “cannots” than “cans”, then starting a new company may not be the best endeavor to pursue. There’s almost *always* a place to begin, and slowly build to something bigger than yourself.

Especially in the digital world – there are talented designers/ developers in our on-demand economy that would love to work on a challenging project.

4) Have clear expectations.

My first year in business, I think I made around $12,000 in revenue. I launched a digital platform for music teachers, and figured customers will swarm in like tourists leaving a cruise ship in Barbados. Yeah, yeah – I read all of the “it’s not a build it, and they will come” sort of thing. But either my over-optimism or ignorance (or a healthy mix of the two) didn’t prepare me for what would come.

The most important thing is setting mental expectations, and don’t give up. Sure – it’s cliche, but nothing rings more true. Nothing amazing comes easy.

5) 60% Digital marketing, 30% CRM, 10% Website.

We hear this question a lot for anyone starting a new company: “I’m wanting to start a new (insert company or nonprofit). I have (insert budget here). What do I spend it on?”

There’s usually a roundabout answer, but here’s a lovingly blunt one:

-Spend the least amount on a site. On Day One – it just really needs to explain who you are, what you do, have great content, and ways to convert visitors to qualified leads.

-Spend a bit more (but not a ton) on a CRM (customer relationship management system) to track engagement and communication with prospects or customers. There’s a ton of easy systems to get up and running quickly (we use Active Campaign, and they’re pretty awesome) – you can always upgrade later, if/when needed.

-Spend most of your budget on digital marketing (aka getting people to your site). There’s a *lot* that goes into this, and not really in the spirit of this article. Site development is part of digital marketing, technically – but hopefully you get my point. 

6) 18 hour work days is a thing in your startup company.

Yup – I’ve read the “work smarter, not longer.” It’s not true. Expect 16 hour days, and even 24 hour days with food and bio breaks, especially in the first year or two. Those hours will dwindle as you grow, but it’s inevitable there’s going to be a lot of sweat equity that goes into crafting your dream. I agree in “work smarter”, but at the beginning, it needs to be “work smarter, and work longer.”

7) Listen to the market and quickly react.

You can do all the market research and develop a product or service accordingly, and then you’re going to realize that you got a lot of things right. And… a lot of things wrong. Leave the ego at the door, and constantly adjust based upon what you’re hearing, and how people are using your product or service.

We started out as a platform for music teachers. Then, a lot of music nonprofits came to us needing help with using digital to raise a lot of money. We created a spin-off of the music platform into a nonprofit platform that combined social networking and fundraising (before Kickstarter). That evolved to being a full-service digital agency.

In 2009, I never planned for any of this, but instead – went where the current took us.

8) Start surrounding yourself with people that make you better

Know your strengths, and capitalize on them. Know your weaknesses, and find good people to fill those roles. Never hire anyone that isn’t smarter than you.

9) Look into coworking.

While we have a fun, lofty office space that allows dogs (and my 2 year old Golden Retriever comes to the office daily), there were many, many days and nights working from a small desk in a 1 bedroom Chicago apartment. The days bled into nights, the coffee slowly transitioned to wine, and 16 hours would go by realizing I’m still in my pajamas. This thing called human interaction would go by the wayside, and it can take its toll.

Depending on where you’re at, coworking is a huge thing, and it’s only becoming bigger. For a monthly fee, you can surround yourself with like-minded professionals starting a company.

Simply bouncing ideas around goes a long way.

In college, think of how much you learned inside the classroom vs. the ‘real world’ college experiences. Going into coworking is like leaving your tiny dorm and surrounding yourself with peers that encourage each other and help push your start up company to the next level.

If your area doesn’t allow coworking, check out local ads for people looking to share their office space.

It beats Starbucks, and your clothes won’t perpetually smell like coffee.

10) It’s competitive. Be nice (and hopefully that’s yourself).

There are zillions of digital agencies out there. While most would disagree with me, I think the supply outmatches the demand. The market has also been flooded with agencies that are focused on the technology itself vs. using it to solve a big business problem. But alas, there are still an abundance of players in this market.

When a potential customer is looking at two different companies to work with, and both companies are equal in terms of talent, timeline and cost, the thing that’s going to separate the two will be personality. Be nice, be willing, and always want to make your customers the best they can be.

What are your tips for anyone looking to embark on their own startup company? Let us know in the comments below!

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Chicago, IL 60613

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