Lessons Learned from Running an iOS Consultancy: Part 1

“Experience is the name everyone gives to their mistakes.” – Oscar Wilde

I’ve worked as an “indie” Mac and iOS developer for more than a decade.

During that time, I’ve worked alone in a basement, a home office, in traditional workspaces, with partners, with teams large and small, started three companies, and lead another.

In the process, I’ve made a lot of mistakes, and learned a ton of lessons along the way.

The most important lesson I learned is not to make the same mistake twice. This article series details some of the mistakes I made, why I made them, and how you can avoid making the same mistake in your own career.

In this first part of a 2-part series, I cover five lessons I learned from running an iOS consultancy:

1. Learn from failure
2. Focus early, focus often
3. Find the right partner
4. Be wary of investors
5. Know when you need help

Let’s dive right in!

1) Learn from Failure

It’s no secret that people tend to learn more from their mistakes than successes. People who seem to find success in every endeavor share a common trait: they recover from failure quickly, get up and try again — often before anyone notices.

Whether it’s software development, business management, creating products, or even personal relationships, we humans have the tendency to learn the more from our missteps than our successes.

As such, I’ve developed a hobby of reading about successful business owners such as Steve Jobs, Richard Branson, Elon Musk and Bill Gates. I’m always reading between the lines to learn the formula of grandeur behind them.

Whenever you can, try to learn from someone else’s mistakes before they become your own — whether they are mine, a family member’s or a game changer’s like Steve Jobs.

2) Focus Early, Focus Often

Before you write a line of code, seek a client, or form a partnership, you first need a focus.

I launched my first “company” during the Mac OS 8/9 era. I gathered a few friends who shared an interest in programming, and we decided to make a game. It was the late 90’s, the first tech bubble was nearing its peak and everything seemed possible.

There were four or five of us, and we loosely decided that we would all have an equal say in decisions. We didn’t even know what we were building before we agreed to build it.

Soon we discovered each of us had a different opinion and no one would agree or compromise on anything, especially when no one was making money upfront.

We finally settled on making a 2.5D fantasy game in the style of Fallout, but had no roadmap, ship dates, feature list, concept art, and no focused plan. Each of us worked on parts we felt were fun or valuable, and in the end, everything fell apart.

The biggest problem was a lack of focus and clear leadership. Since each of us was only working for future profits, there was no incentive to back down. Each of us thought his or her idea was the best.

With no leader, no money, no focus and no plan, we were just running wild. Stress levels rose and people began to focus on other projects. Soon we all abandoned the project.

The one saving grace of our failed experiment was we were all a little wiser, and for me, I understood the importance of having a focused plan.

3) Find the Right Partner

A business partnership can be a wonderful thing. He or she can motivate you when you’re exhausted, be a sounding board to bounce ideas off, boost your confidence in what you’re doing and be an anchor through the ups and downs.

However, you must choose wisely! The right business partner will force you to grow, constantly challenge you to improve and help you elevate your company to new heights. On the other hand, the wrong business partner will drain your energy, burn you out and/or damage the business and leave you holding the bag.

Friends and Family: Not the Best Partners

Partnering with friends or family might seem appealing at first, but prepare yourself for those relationships to change in ways that might not be positive. The old adage, “Never hire your friends” applies to business partners — tenfold.

Driving a business is hard enough without complicating it with personal matters that come along with working with family or friends. It’s too easy to overlook or brush aside a friend or loved one’s flaws and shortcomings, or worse yet, stuff your concerns back down inside rather than addressing them early.

However, when stress levels peak, you’ll have fewer filters and your concerns and frustrations will surface. The relationship will never be the same after that happens.

For an example, look at Penn and Teller — yes, the magicians — who have a solid partnership that spans almost 40 years. They claim their secret to a solid business partnership is not being friends. They rarely hang out outside of work and keep their personal lives separate, and it’s effective for them.

Choosing the Best Partner

Find a business partner from outside your social circles that shares your vision and values, and above all else shares your work ethic. If you are the type of person who works 16-hour days, make sure your business partner is too. When one partner works harder than the other, or at least it seems that way to one of you, the interpersonal dynamic and communication can deteriorate quickly.

You want to get it right the first time. Parting ways with a co-founder is not an easy task, especially when there’s money (and egos) on the line, so do your due diligence during vetting, and make sure to document all your agreements and plans in order to set clear expectations for each other and your business.

4) Be Wary of Investors

Finding investors for a consulting company is a hard sell, especially before you have income, products or a track record. Unless you’re lucky or have easy access to start up funds, you’ll probably need to bootstrap the company yourself.

In the event that you do have interested investors, or choose to seek investors early, make sure you understand what you’re getting into.

Understand the Investor

An investor is a business partner with a single focus — the exit. They’ll push you to be profitable and sellable early on, even if it means you have to take steps that are not in your interest, or conflict with your vision for the company.

When you take on an investor, you trade equity in your dream for cash early on. So ask yourself: If you really believe you have a billion dollar concept, do you want to trade 30% of it for a few thousand dollars and a lot of pressure?

Later stage investors are more common for consulting companies. As you expand your business, increase your profits and experience success, investors that want a piece of the pie may approach you.

On the positive side of the equation, these people can bring more business, marketing power, advertising budgets, networking opportunities and even just good advice. However, they can also start arguments, bring woes and demand unexpected changes in direction.

Think Before You Leap

Before you dive in with an investor, it’s crucial to understand what’s in it for him or her and anticipate the inevitable exit strategy. If his or her goals and motivations don’t align with yours, there will be many bumps in the road.

A single question has helped me make tough decisions about bringing in an investor: “Is this the right move for the business, the clients and the employees?”

After carefully weighing everything, I have to be able to say yes to all three. Otherwise, the influx of capital isn’t worth the hassle.

5) Know When You Need Help

A cliché about business ownership is that owners “wear many hats.”

Especially in the beginning, you’re the defacto accountant, legal department, bookkeeper, human resources manager, design team, development team, manager and every other role the company needs. Likely, you’ll do a few well and the rest poorly.

Eventually, you’ll find your breaking point and you’ll have to start deciding when to hire and whom to bring onboard to fill these roles, and whether it’s better to hire vendors, contractors or employees.

Giving up profit for resources and help is never an easy decision, especially when the helpers don’t directly generate revenue. Waiting too long will bite you, and not waiting long enough will bankrupt you.

Get Help Protecting the Business

Unless you passed the bar, a lawyer is likely to be one of the first roles you need to fill. Many years ago, I thought I was smart enough to review my own contracts and that my limited cash flow shouldn’t go to a lawyer who bills $200 an hour. Like many others who’ve been in there, I made a mistake that cost me much more than a lawyer would have.

Here’s what happened: there was a clause in the contract that reduced my total payment by 5 percent for each day the project was delivered late. So if the project was 20 business days late, I would receive no payment at all.

When I negotiated the contract, I noticed the term but felt confident I would deliver on schedule. As the deadline approached, the client — who was responsible for design — had not delivered. When they finally handed it off, it was too late to finish on time.

I delivered the final product almost a month late, due to no fault of mine. Because of the wording in the contract, I received no payment and had no recourse.

For more than three months, I worked for free.

A fair contract would have set terms for both parties’ deliverables, and a good attorney would have advised me of the same. I thought I could be my own counsel, but my lack of experience and knowledge ended up creating a problem that bit me hard.

Don’t Wear More Hats Than You Can Fit on Your Head

A single line in a contract can really harm your company, be it indemnification or payment terms or other clauses.

Likewise, a miss on a line in your tax returns can cost you your entire life, and poorly composed marketing copy can make you look inept to potential clients. Really, there are endless problems that can arise from donning too many hats.

If you’re like most entrepreneurs, you’ll need to make a misstep before you realize you need help — it is a hard thing to see coming. These types of mistakes can cost you a lot, even your entire business.

Learn to admit when you’re in over your head and need help in one form or another. There is no shame in it, and you literally can’t wear all the hats, all the time – as fashionable as that may be. :]

Where To Go From Here?

I hope some of this advice has been helpful for you – hopefully you can avoid some of the mistakes I’ve made! :]

Stay tuned for the next article in the series, where I’ll cover some tips on scaling, communication, networking, and more.

In the meantime, if you have any questions, comments, or your own lessons to share, please join the forum discussion below.