Transitioning from solo founder to startup

Every business was once a single person with an idea. Some companies stay that way of course, but most founders will inevitably reach a point where they need help from others. If not before, then at the time when they’ve finished building a product, found a foothold in the market, and their natural next step is focusing on growth. 

I was super lucky starting out. My first company was an accident: I’ve built a system that made it easy to build websites, at the exact time people wanted websites but couldn’t get one. Without any marketing or sales, I’ve seen a queue of people who wanted my software.

The orders kept coming in and the order sizes kept increasing. As a founder without much help or mentors, I was up to my neck with work. I never said no to anyone. The only thing I did to manage the workload was to keep increasing the prices. Unfortunately that didn’t keep anyone away, and I found myself in bigger trouble.

Cloning yourself would be such an amazing solution to all these problems. I’m thinking of the cinema type of cloning, where you get another person with the exact same memories. Your clone could get to work right away, without training, knowledge share or any other management overhead.

As you may have guessed: one of the most useful things I’ve learned on my entrepreneurial journey is the importance to delegate.

Employers gonna employ

One reason why it’s such a difficult undertaking to run a company is the large number of entirely different tasks you need to do.

Most founders are drawn into the business by the most creative tasks. Creating the product, the brand identity, or the marketing messaging is great fun, at least for the first time around. Taking care of taxes and paperwork, the terms & conditions -- that’s only interesting for a select few.

Having to learn a bunch of things in a short period of time can be addictive. And in other times, you need to be frugal and deal with everything on your own. But sooner or later always comes a time, when the tasks you don’t enjoy doing can be simply outsourced.

Outsourcing can mean many things, but it’s usually one of these:

  1. Procurement. You may be able to find a product or service out there, and just buy what you need. Purchasing something off the shelf is usually the simplest and easiest to do, if you can find a product that fits your needs exactly. Unfortunately it’s often prohibitively expensive to do so, or impossible for time constraints, legal or other reasons.

  2. Agencies and freelancers. For things that need to be more custom made, you’ll need to hire someone. Working with freelancers and agencies is a great option to get started, because it’s easy to scale it up and down. You can buy exactly as much as you need: hire someone only when you have more work to do. Without an employment contract or retainer, you don’t need to pay others when you can handle the work yourself.

  3. Employees. One issue with freelancers and agencies is that the people you’d like to work with might not be available when you need them. Hiring someone full time or part time solves the problem -- and it also creates a few more, including legal obligations, management and organization overhead.

Of course there are many other options out there, and hiring help is not as black or white as this list makes it seem. To mention two more common options as an example, contractors are a crossover between freelancers and employees, and interns are junior employees with a huge pay cut. The takeaway here is that everything works, as long as you can align motivations, and keep everyone happy.

Getting started with management

Management is hard, because it involves a whole set of skills that you can’t learn in schools. You’ll have to rely on your instincts, and most of us don’t have helpful instincts managing people.

Just like tennis, the only way to be better at leadership is by doing it. In tennis you’d need to find a partner, a court, and then go out to start improving your forehand. In business, you’d need to find a task to delegate, someone to delegate it to, and start improving the workflow.

It’s literally how everyone does it. As soon as you ask someone to help you with your task, you graduated as a manager. And the more opportunities you have working with others, the better manager you’ll become.

Learning to delegate is an acquired skill, but it’s core to running a successful business. The only real question is, where would you start learning to delegate? Here are a few quick tips for your first project:

  1. Keep it small, and delegate something you could do well yourself. You can experiment with these things later, but you can learn quicker with a short turnaround project. For example, get someone to write specs for your app idea. Or find someone to pick up your phone. Or someone to do the research for your homework. Then write out in detail how people should help you.

  2. Look for freelancers first. Employment is messy, and you won’t learn much from agencies. Hire the first person who looks a good fit for the job, don’t waste much time interviewing and making that decision. It’s really hard to tell freelancers apart from their pitch alone.

  3. Write a great job description. It should include the deliverables, time frame and everything they need to successfully finish the task.

  4. Start the fixed rate contract with a tight deadline. Everything over a week or two is too long. When the freelancer is underway, don’t walk away from a task. Micromanage the schedule and each deliverable for this test project, to learn the most about the process.

The first experience with delegating anything meaningful will almost certainly cause pain. There are a zillion ways where things can go wrong: you may have carefully explained everything, but then it turns out that it’s all lost in translation.

That’s a good time to learn from the experience and the feedback, and try again.

Outsource everything

When people ask what they should outsource, my best answer is that you should outsource everything you can. Your best contribution to society is all the things you’re best at, so you really shouldn’t do anything that other people can do too.

The long term dream is to be able to delegate everything other than your best work, but for now, start with a low risk task. Start small, and gradually work your way up. Don’t worry if outsourcing the first few tasks takes more time than it saves you. Consider that an investment. It will open the door to ultimately assign everything else to others, saving you all the time you need for even bigger projects.

Delegating is a super power and it gets easier with practice. You’ll be better at it with every successful project and every new hire. Just start anywhere.