10 Lessons Learned as a Web Entrepreneur

This post is based on a talk I gave earlier this summer at Twin Cities Drupal Camp. Listen to the recording here.

My journey of discovering the web began in Japan in the late 90s. I was living and working in Takaoka as a high school english teacher and our school was able to participate in an early pilot of internet connectivity that fascinated myself and my students. Suddenly, learning a new language came alive for them as a way to communicate with anyone, anywhere, at any time.

Flash forward a few years and I was back in the states looking to build my future along with this whole internet thing. I became a web developer at a Dot Com startup and then eventually decided to cut the safety ties and branch out on my own. I built a team of amazing people and together we built an incredible portfolio of work, happy clients and successful projects.

Along the way I learned a lot of lessons. These 10 are the most important things I wish I had learned sooner, including some things I’m still mastering:

1. Change is Opportunity

Change is ALWAYS an opportunity. Sometimes change can be hard and challenging. But instead of letting it frustrate you, train yourself to step back, analyze what is different and search for the opportunity in that change.

When I started out on my own, my first big client was a syndicated TV series on PBS. Together we designed and built a great site. Their first season with the new design and features were a huge success and we had big plans for our second season together. I loved the project and people and knew that the national exposure was a great thing for my future.

Then, as we prepared for the next season, the show was canceled. At the time, I was devastated. The client represented job security and a great portfolio piece, and now it was gone.

I didn’t realize it at the time, but this was actually one of my greatest opportunities. When the show was cancelled, the folks I had worked with needed to find new work. Once they all settled into new jobs and found themselves in need of web help, they called me. Instead of one great client, that team introduced me to at least twenty great clients.

Change is always opportunity. Train yourself to see it and you’ll go far!

2. Ask Basic Questions

Be brave enough to show the holes in your knowledge. Basic questions have a way of getting to solutions, bypassing jargon and vague, hand-wavey answers.

Once, we took on a project for a major architectural firm that had offices around the country. That group was among the most intimidating group of people we had ever worked for—they were incredibly well-versed in design and engineering, and how to make things work for real people. They wanted to push boundaries and make beautiful experiences.

As we got deeper and deeper into the project, we often had to mediate between disciplines and handle conflicting feedback from people who were all too important to ignore. The only way we could do this was by continually returning to basic questions: Who is our audience? Why will they care? What is more important? Who will maintain this?

Those basic questions keep people grounded and focused on the fundamentals at hand. Even when you think you know the answers, getting others to answer basic questions will always improve everyone’s understanding of the problem at hand.

3. Charge According to Your Goals

Many of us struggle with how much our services are worth and how much we ought to charge. It’s a frequent topic of conversation among business owners new and old alike. We frequently wonder if our prices are too high or low.

When I first started out, I didn’t charge hourly rates. I didn’t want to track hours. I wanted to provide more value than I charged. I talked with each client to figure out the scope of a project and what it was worth. That mindset was a great balancing force: It kept me focused on what was valuable for us and the client.

It’s important to make peace with the fact that you will never charge the perfect amount 100% of the time, or even the same amount for similar work. You may charge more for a job with a client who is hard to work with, or less if it’s a project that lets you explore a new skillset.

When your rates are in line with your goals, you will be more enthusiastic and effective. You will demonstrate your value to each client without selling yourself short.

4. Keep Growing

We’ve all heard the platitude ‘grow or die’. It’s true, but not in the way you might think. Too often, companies read that as “add staff or die.” But there are plenty of other ways for your company to grow. Grow your skills, the services you offer, new innovations in your industry--all of that growth can keep your company alive and moving forward.

At a certain level, though, it does make sense to add staff. At Gorton Studios, we kept our team to just seven people for years. We grew our skills, we grew our profitability, we won bids for top end jobs with our tiny team. Our numbers looked great.

But we also had to go back and do legacy work for older clients. It was tedious stuff and wasn’t what we loved. If we had brought in new people, they could have taken on some of that grunt work, learned new skills and allowed our senior team to focus on progressing the company. As it is, that backlog of unfun instead work led to burnout for me and others.

If you want to thrive, keep growing. Keep improving what your team can do, what you can do, and bring in new blood when things start to get stale.

5. Take Care of People

If you do this, the rest will work out. If you’re generous with your time and treatment of others, you can get more out of a situation than you would by just serving your own self-interest.

At Gorton Studios, I spent a lot of time on the phone with people who had great ideas, but not enough budget to hire us. I would spend the time trying to help them fit their idea into their budget, always with the intention of helping their organization succeed. Then I’d refer them to smaller agencies that were a better fit.

Helping those people who weren’t in a position to return the favor ended up being a major part of our firm’s success. The smaller agencies I referred clients to would send referrals my way if they got a project too big for them to handle. And sometimes the clients with a small budget got bigger, and they came back two or three years later with a new project for us.

So be open, be willing to help, and put into the world what you’d like to get back from it. It’s good karma and good business.

6. Be Honest

The world is watching. Web professionals succeed or fail based on our reputations. We’re fundamentally a human-powered business, where the individuals working on a project define that project. In that environment, there are few things more damaging than a tarred reputation.

Take it seriously. If you don’t know something, admit it. If you should have known it, you may be embarrassed about that. Either way, you’ll have learned something—and continuing to learn is a critical part of success in this industry.  

At Gorton Studios, I extended that honesty to the inner workings of the company. I shared our financials with my team and this transparency helped bring us together. We all knew which projects we made less money on because we loved the work, and everyone felt better about the boring projects when they knew how those projects contributed to the bottom line.

That doesn’t mean you have to present each client with your entire financial history—there is plenty of information that you should keep within the company. But honesty and transparency will serve you well in your business and personal transactions.

7. Say No

The more often you say no to the wrong project, the more available you’ll be to say yes to right project. You’re going to find success only by finding the things you love and can do the best, so be selective with your work and do the right things really, really well.

As soon as you can say no in your business and get away with it financially, make it a habit. The more you say no, the better your profit margin will be. You will develop the ability to focus on an industry or technology and really excel. If you hate doing e-commerce and there’s no future for you in that field, say no to people who want you to build an e-commerce site. On the other hand, if you’re innovating in e-commerce and building a fantastic skillset there, say no to projects that don’t include e-commerce.

As you build the career you want to have, ‘no’ is going to be one of the most powerful tools you have. Use it to define who you are, what you do, and how you’ll succeed.

8. Follow Your Passion

Your path as a web entrepreneur will always have its ups and downs. If you’re doing something you’re passionate about, you’ll make it through. You will be willing to put forth the effort to create extraordinary things. Your passion will carry you through the rough spots. You will get better at what you’re doing; you will learn to avoid mistakes and solve problems.  

Figure out what you like to do and what you’re great at doing, and focus on that. It will create success. If you just wanted to pay the bills, you wouldn’t be an entrepreneur. Something drove you to strike out on your own. Keep pursuing what matters to you. Keep challenging yourself to pursue your passion.

9. Trust Yourself

You need to trust yourself. Trust that you know enough to succeed because if you’ve made it to this place, and you have the knowhow to make good choices.

It’s important to get advice from others, of course, but just because someone doesn’t see the merit in your idea doesn’t mean it has no potential. I’ve found the best solutions come from collecting advice from others and combining it with my own experience and instincts. That way I’m not blindly following someone else’s advice or getting stuck in my own head--it’s a good way to synthesize new and interesting ideas.

So take other people’s advice into consideration, but when it’s time to commit to the big decisions, go with yourself. If you go with yourself and lose, you learn, and you’ll do better next time. If you win, you win. Both are good for your future.

10. Do It

Nike got this one right. It’s easy to spend too much time talking, analyzing and planning. Eventually you have to just do it. You will never have all of the data to make a decision with absolute certainty. Risk is part of the package.

Do you have an idea? Try it. Get it out in the world and see how it does. If it fails, make it better. If it’s a massive success, make it even better. No one is going to make things happen for you except you.

These are just 10 of the hundreds of lessons being an entrepreneur has taught me, and I’m still learning each day. We all have your own lessons to learn, but if you can stay confident, humble, honest and passionate you’ll do great things.

Go for it!

Topics Agencies, Digital Agencies, Education, Agency Partners, Drupal