10 Things I’ve Learned From 3 Years of Running A Business

I’m coming up on the three year mark of running my own business. I still have a lot to learn, but these are ten things I’ve found to be true for entrepreneurs.

1. No one in the market owes you anything, and you don’t owe anyone else anything either.

The market is a ruthless place. If you want to form alliances with partners, investors, or complementary businesses, it has to make sense for both sides. No one is going to enter into any sort of deal that only benefits one side.

Likewise, consumers must see the value in your offering in order to become customers. If they do not see the value in what your product or service offers, either the value doesn’t make sense to them, or you haven’t described the value adequately.

Just because you show up, doesn’t mean you’re guaranteed success.

2. Only those who have gone all in as an entrepreneur know what that feels like.

Starting a business is an emotional roller coaster. Just check out all the think pieces on Hacker News or Medium and you’ll know exactly what I mean.

It’s a soul-crushing gambit, which you have to be mentally and emotionally tough to endure. Find other entrepreneurs who are at a similar level to you (or one step above) and form an accountability group. By being around other people who have gone through the same things you have, you’ll be able to help each other by supporting each other by sharing your experiences and knowledge.

3. Your competition will bring their best against you every day. It’your responsibility to bring your best to the battle as well.

Even your friends who are in the same field as you are your competitors.

While it’s good to form alliances whenever possible, never forget that at the end of the day, people are all about doing what’s best for their business.

Iron sharpens iron. In order to be around people who are influential in your space, you must constantly be upping your own game.

Never quit grinding. Never quit being hungry.

4. There will be people close to you who try to dissuade you from your path. Carefully consider who you listen to.

This is a common one. When you break away from having a day job, and set out to start your own business, your friends or even family members may try to talk you out of it. They may bring negative mojo whenever you mention running a business to them.

To me, this is a real “Mom I love you but this trailers got to go” type of moment.

I love my friends. I love my extended family. But starting a business for me was not only the best option for my circumstances, but something I had to do. It’s something I went all in on.

Many people close to you won’t be able to understand this — ever. And that’s okay. It doesn’t mean you stop loving them.

However, I will say this. If your immediate family, your spouse and children, aren’t on board with you starting a business, you will never succeed. This is a big life step, and your spouse needs to be 100% on the same page with you, or you are headed for troubled times.

5. You can’t control anyone but yourself.

This one is more of a general life principle, not limited to business.

Simply put, you have to be okay with the fact that people will do whatever they want to do, and you have no control over that.

You can’t base your own happiness on what other people will do or say, because you can’t bend someone to go a direction they don’t want to go.

The most you can do is state your case, and see if you can convince them to get on board with what you believe in. Don’t count on anything outside of yourself, though.

6. No one matters outside of your family, your team, and your customers.

Thanks to Cory Miller of iThemes for this one.

Your family is the foundation of any success you have — in business, in this life, wherever. They have to come first when it comes to any major decisions.

Your team is who you depend on to build your collective vision. You’ve convinced these folks that your business stands for something that they believe in. Something they believe in enough to spend half their waking hours (or more) working towards. Together, you share a vision, and you work together to see it come to fruition. Protect these people. Your success depends on theirs.

Your customers are your evangelists, your brand ambassadors, the people who pay the bills for your company. Always make sure you deliver on your promises to them. Give them the value they expect, and treat them like gold. They will help your company grow into the future.

7. No one sees the grind or how long it takes to get to success, they only see the final result.

Everyone has heard the stories of the ten year overnight success. That grind, paying your dues, and building a business, day by day isn’t just good copy — it’s how every successful entrepreneur found their path.

Don’t shy away from rolling up your sleeves and doing the work, for as long as it takes to get there.

8. No one else has your DNA.

Successful companies distinguish themselves through their philosophy, their culture, and their actions. No one else has the same set of experiences as you do. If you’re a founder, that DNA will permeate your company culture.

Be more of who you are, not less. That’s the way to distinguish yourself in a crowded market.

9. Failure isn’t the end of the world.

As long as you’re alive, ’ll always have another chance to try again.

Failure is the predecessor of success. Fear of failure is what keeps most people from starting a company or striking out on their own.

But all of the entrepreneurial heroes in the history of the world endured many failures before finding success. That doesn’t mean fail like an idiot, but what it does mean is to be fearless when it comes to risk and failure.

10. Just keep swimming.

Perseverance is an essential trait if you want to start a business. Like Gary Vaynerchuk says, most wannaprepreneurs take one punch to the face and slink back to getting a day job.

Starting a business of any size is inherently risk-laden.

There will be days where you wonder what you got yourself into. There will be emotionally difficult days.

Block all that out and just keep moving. Keep grinding out victories.

History is written by those who are too stubborn to quit.

Starting A Relationship With A Web Consultant

If you own or manage a business, you probably already have a website.

What you might not have is an ongoing relationship with a web consultant, developer, or web agency.

The vast majority of small business owners get their website built, and they and their developer go their separate ways.

It may be a year or two until the business needs an update to their site, or a related service, like site redesign or SEO help.

Oftentimes, the developer has disappeared, or the agency may have ceased operations.

Finding a strategic web development partner is difficult the first time. Imagine having to do this every two years. Ugh.

Because finding a web consultant isn’t something most folks have to do all the time, they may not know how to go about it. At best, they may make some of the same missteps that they did in previous searches, and end up back in the same position that they were before.

I’d like to offer some helpful advice on how to start a relationship with a web consultant in a way that won’t leave you stranded again in a couple of years.

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Are You Buying A Website Or A Relationship?

There are millions of studios that provide web design and development services. It’s hard to differentiate what makes one different from another.

Or is it?

Most web shops that survive for a long time have some sort of differentiation. Either they are good at graphic design, or a particular type of development, or a certain form of marketing.

But there’s another factor that very few people talk about.

The web studios that thrive over the long haul do more than exchange services for money and then disappear. They establish an ongoing relationship with their clients — one that lasts many years.

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The Importance of Margin

When we talk about margin in our business, we instantly think of profitability. But there are several kinds of margin — and several of them are enabled by being profitable.

As long as a business is sufficiently profitable, it can remain viable. To be a little profitable is not enough to ensure long-term survival, for a number of reasons.

There are factors that are in your control, and some that are not.

Longevity is based on anticipating the factors that are out of your control, and planning for them. The ongoing fortunes of your business also depend on maximizing the things you can control, and being aware of what actions you need to take.

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Outside Our Bubbles

My friend Mario is a bad-ass programmer who works with enterprise level clients on WordPress projects. He has talked frequently about how 99% of the WordPress community is not heavily involved in keeping up with best practices and what’s going on. He correctly states that only about 1% of the community contributes back to the growth of the platform.

I would argue that many communities in the larger tech space are like this. The Apple ecosystem is vast, but very few people contribute to the actual advancement of the platform. In the larger web development community, there are a larger number of active contributors, but many people are essentially end users, doing their daily jobs.

Of each of these communities, the voices that guide the community as a whole are perhaps 1% of the 1%.

This isn’t right or wrong, it’s just that once you get recognized as moving the needle — whether that’s page views, downloads or selling conference tickets, you’re going to continue to get booked.

Most people who gradually reach the point where they are seen as community leaders wholeheartedly deserve it. But the people who keep coming up with new ways to share what they have learned have the most longevity.


Every community has a sort of culture bubble. It doesn’t matter if you’re talking about tech, politics, sports, or popular culture. Every community — every tribe, if you will, has an ideology bubble.

I have seen a few notable people in the WordPress ecosystem talk about learning from other programming communities. Tom McFarlin, Mendel Kurland and John Eckman are just a few.

Not only does each community have an ideological bubble, but as individuals, we each have a bubble of what we expose ourselves to.


As individuals, we continue to evolve through our lives, based on our experiences and what we are exposed to. Most of us go through several shifts in our thoughts, approach and demeanor while staying true to the “core” essence of ourselves — that which makes us unique, and cannot be separated from our being.

But one thing I’ve noticed as I get older is many people begin to limit what they expose themselves to as they mature. They cut off their opportunities to learn from others, perhaps for fear it will change what they believe their core essence to be.

Our identities are really about our beliefs, our knowledge, the affinities we have, and our philosophies about life.

When we restrict our ability to reassess what we believe in and why, we risk becoming stagnant. In this industry, that is lethal.

As a personal challenge, I encourage you to step outside of your comfort zone. Read something, listen to something, do something that you have been putting off exploring.

Expose yourself to different voices — ones outside of the particular communities you have built your self-identity around.

Realize that you can learn from anyone, even if you think they have nothing to offer. You may be surprised where life takes you if you let it happen.

Why I Don’t Recommend Freelancer Marketplaces

So much of what makes a web project successful is the communication between the consultant and client.

When there is trust between both parties, communication is more honest and open.

So, before I even agree to take a project, this ability to communicate — this connection — is something I’m looking for.

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Building Your Website On Stable Ground

Web design is one of the more ephemeral forms of design.

The things we build very seldom stay unchanged throughout time.

Times change. Technology changes. And most importantly — the needs of the people using your website change.

A website is never truly finished. It is a constantly evolving organism.

How a website evolves depends a lot on how intently the architects are listening to the people using the site.

The Only Thing Constant Is Change

Every so often, there seems to be an upswing in the number of people who are actively seeking to get their website redesigned.

Sometimes, it is brought on by news that websites will get penalized in search results if they don’t comply with basic usability requirements.

I know that many of these websites should have been designed with usability in mind from the get-go — whether that means accessibility, mobile-friendliness, or page speed and performance.

Whatever the reason that business owners seek to improve their websites, I’m happy that they are motivated to do so. There are a couple of reasons for this.

Website redesigns, when done right, can have a huge impact on the bottom line of a business.

Customers trust sites that look current over those that don’t. That’s one place conversions can improve. (By conversions, we mean taking an action, like signing up for a newsletter, or buying an item from an online store.)

Page speed affects conversions. So does mobile-friendly design.

But a lot of site owners are not savvy enough to make changes or updates on their own. Many sites don’t have any sort of analytics installed, so observing how customers actually use their website is impossible.

Some site owners are locked into old technology, and since it’s been so long since they had their website built, the web designer is long gone.

This can be overwhelming.

But all is not lost.

The Web Is Malleable

Web design is a constantly evolving form of design.

In almost every other form of design, once the artifact is made, that’s it. It’s done. Game over.

If an architect designs a building, once it is erected, it’s finished. There is no easy way to redesign it.

You can maintain a building, but it’s difficult to reassemble it, and not disturb all the people working inside of it.

But here’s what is so great about web design as opposed to other forms of design.

You can rebuild a site to make it easier for people to work, shop and do what they need to do, if you see a problem. You can even rebuild a website on a better foundation to make it work better, now and into the future.

Your site doesn’t need to be an inflexible monolith, that can never be improved. It can work for you &#8212 to better satisfy your customer base.

Redesigning With Purpose

Like the Frank Lloyd Wright quote says, nothing can be built without knowing the needs and use cases of everyone involved. That means the site owners, the people who maintain the structure, and the customers within.

Owners are sometimes baffled why I ask so many questions about their business. Why do I ask?

The more that I can know about the business I am designing a site for, the better I will be able to help them achieve their goals.

The goal is always to improve your business by making sure your website fully supports your business objectives.

Your website should be your most tireless and efficient employee. I need to know what actions the business profits from, so the website can assist in those tasks.

Hearing customer input also helps me determine what areas of a current website need the most improvement. Sometimes there is functionality missing, that customers wish was there.

Making your business website appealing and easy to use signals to customers that the business is trustworthy. Making sure the customer can find information or complete tasks they came there for means more sales for the business.

An empty building and a website with no visitors are both equally useless to the owners.

Gathering Information For A Flexible Future

The great architects of the past didn’t design their blueprints in a vacuum. They gathered as much information as they could — about the land they would be building on and who would be using the building. They had to know the constraints and limitations of the building site, and consider the needs of the tenants and landlords.

But what if those needs change over time?

As web consultants, we are used to design trends, marketing techniques and technology changing constantly. Change has been the one constant of the web.

When the needs of your business evolve, you don’t want to tear your whole website down to the ground and start over.

At the same time, you need a web structure in place that will adapt with your needs. Something that will scale with your business, so you don’t need to start from scratch every few years.

The best web designers will help you solve the issues of today, but will also build with an eye to the future. They know your website will continue to evolve, and they will plan for tomorrow, and not just the present moment.

The web consultants I respect talk more about business goals than they do web technologies, but are masters of both.

There are multitudes of people who can build a website, but few who can help you build your business. There are plenty of people with access to the tools, but few who build on stable ground.

Leveling Up Your Business Website

Every business goes through a growth curve when they begin.

Some businesses succeed, and end up having longevity. Some of these reach a sweet spot where sales are about the same, year to year. Others continue to grow and expand, year after year.

What is the difference between the business that hits a plateau, and the one that continues to grow?

What factors can help a business level up? What things can hinder growth?

Obstacles To Growth

Leveling up is not for every business owner. Some are happy to get to a certain place and not go beyond it.

I am happy for them.

For businesses that want to continue to grow, they’ll have to make certain changes at certain points. These are not always easy or comfortable. But sometimes, stepping outside what is familiar or routine produces the greatest results.

Leveling up your business means doing things a little differently than you did in the past.

What got you this far won’t get you to the next level.

What You Aim For Is What You Achieve

There are businesses that have a steady flow of revenue, that doesn’t go up or down. They are satisfied with that. They don’t wish to grow bigger, and for them, things are fine.

Many of these businesses see the idea of a professional website and marketing as expenses to avoid! They do not see these things as an investment in their business.

Word of mouth has worked for these businesses for many years, so they see little reason to change.

The problem is that word of mouth only travels so far and so fast — and things don’t stay the same forever.

New competitors open in their service area. People in their existing customer base move away, retire, or no longer need their service.

Over a long period of time, this erodes their customer base.

So where do new customers come from?

Growth Is A Mindset

There are businesses that desire growth. They look at a professional website as an investment, and spend time each month marketing to potential customers.

These business owners realize that, fair or not, customers judge the trustworthiness of a business by their website.

Sure, a business owner can save a few dollars by spending weeks trying to build their website themselves. They can cut costs by hiring someone for $10 an hour from a freelancer exchange.

But in both those cases, their site will likely turn off more customers than it attracts, not to mention be vulnerable to malicious hackers, and not optimized for search engines.

Businesses intent on leveling up don’t build their business or marketing platforms on shaky ground.

Quality Influences The Outcome

It’s normal for business owners to research potential business partners, employees and vendors. This should be the same for who ‘re choosing to plan your web design, development and marketing efforts.

  • Who works there? Who will actually be doing the work?
  • What is their experience? What’s the background of the leaders there?
  • What results have they achieved for other clients?
  • Does their own website look polished or does it look behind the times?
  • Do they teach others what they know?
  • Are other clients giving them positive reviews?

These criteria seem like they would be universal. But there are numerous web design sites that are not mobile-friendly, some of the portfolio sites no longer exist, or the people behind the work are an unknown quantity.

Your Website Represents Your Business

Customers may not trust your brand if your website looks old or doesn’t work as expected.

Likewise, potential business partners and investors will be less likely to trust your business if your website sucks.

A Stanford University study showed 75% of people judge the credibility of a business by the quality of it’s website design. According to a ResearchGate study, people thought 94% of businesses with a well-designed website are more trustworthy than similar businesses with poor website design.

It’s difficult for potential business partners to take your business seriously if your website is outdated, or looks like your nephew put it together.

Leveling up your business also means investing in your online infrastructure.

Go Far Together

If you have no website at all, a brochure website might be a good first step, but it ‘t be your last step.

You’ll need an ally in your corner, who has the ability to help you, and who wants to see you succeed.

If you have a business website that is no longer serving your needs, then you should consider not only today’s needs, but tomorrow’s needs as well.

Building a website for stability, expansion and extensibility means it will be easier to level up in the future.

Choosing a web development partner is as important to your business health as choosing a doctor is to your personal health.

Consider the things you value most in your business. Research and find a web design provider who also values those same things.

Websites are never truly completed. Find someone you can work with, who has the aptitude and knowledge to take you to the next level.

Give More To Win More

This idea is so good, I wish it were mine.

But I’m happy that it’s out there.

This simple idea plays to our human desire to win — at business and at life.

It’s difficult to succeed at any endeavor without allies. You need people behind you who want to see you win.

How do you motivate people who with you and for you to over-deliver? How do you gain allies in a hyper-competitive landscape?

The answer is simple.

You have to give more in order to win more.

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Connecting With Clients

Web projects are most successful when there is clear and open communication between consultant and client.

When there is trust between two parties, communication is more honest. So, before I even agree to take a project, this ability to communicate — this connection — is something I’m looking for.

Here’s some of the things I’m asking myself when evaluating a prospective client:

Will I get along with you? Is your project a good fit for my expertise? Is there someone better suited for this project? Can I deliver multiple times the value you are investing?

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