The Bootstrapper’s Plight: The Social Headaches of Building a Business

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This article is part of The Survival Stage section of 📕 Zero to Sold: The Bootstrapper’s Compendium.

Many founders choose to create a lifestyle business. They have read the 4-Hour-Workweek by Tim Ferriss and now want to build a company that can sustain a life of travel, enjoying the world, and spending time with their loved ones.

Gone will be the days of overtime, the excruciating commutes, the pointless teambuilding weekends.

Well, eventually. And maybe, quite soon. But for most founders of a bootstrapped company, there is a lot of work to be done first. And that work takes time.

In this article, I will talk about how your life might change after leaving the safe confines of gainful employment to work on your own business. I’ll show how conversations with friends and family can change, how to deal with people who just don’t understand that what you are doing matters and where to look for people who share your struggle.

You will build your lifestyle business eventually. This guide will help you get there without running into the social obstacles that come with entrepreneurship.


Welcome to life as a bootstrapped founder. It can be exhausting and tiresome. But it sure is fun and rewarding. Like all things, building a business has good times and bad times.

Founders start businesses to create value and a better life for themselves and the customers they serve. But founders are not ordinary people.

Most people work to pay the bills. They get paid every month on time. They make just enough to cover their expenses, and when they get a promotion, their expenses rise with it. If they’re disciplined, they will save a little money here or there. Pension plans will take care of their retirement needs. They work five days a week, eight hours a day, maybe some overtime here or there. When they get home, work is over for most of them.

The moment you become a founder, this all changes. 

If you are bootstrapping a company, you will not have a regular income for quite some time. You won’t save any money, as you will pour it into your fledgling business. You won’t have the means to contribute to any retirement plans at all. You will want to work on your business every day. For most founders, work begins the moment they wake up, and it ends when they fall asleep. It is a very different life.

When you come from a regular job, becoming a founder will lead to a significantly different life. People who understood you and your choices in the past suddenly start to change. They might try to discourage you. 

Here are a few conversations you might encounter as a freshly minted founder.

The “This Is Too Risky” Conversation

Some people think that you should not have too much control over your own destiny. It seems risky, and it actually is. That is a scary thought for people valuing security. They will tell you that working for someone with a plan is a good strategy. To them, self-employment appears selfish and egotistical. Job security ranks higher on their priority list than job satisfaction. 

These people fear you may succeed.

The “But What About Your Career” Conversation

You’ll start having conversations with people who feel that the career as an employee is the correct socially upward move. Getting out of your expected career path to chase a dream seems indulgent and irresponsible to them. You may hear comments comparing you to impoverished artists and failed visionaries. They usually mean well, they want to protect you.

These people fear you may fail. 

The “Why Would You Want to Do This” Conversation

Others will have no conception of what a founder is. They will assume any number of things that are not even close to your reality. They might think that now you will start wearing a suit and pitch to TV celebrity investors all day long. They might think you’re just another kind of manager, like their boss, just for your own company. Conversations with these people will focus on the mundane, the unnecessary parts. They won’t understand the scope of your vision, as they could not envision themselves to follow such dreams. They will tell you to be careful, as they think no single person could ever be capable of that. 

Those people just don’t understand.

Some people just value their 9-to-5 jobs and free weekends. That’s a perfectly fine position to take on life. But a founder will not take that position. Not taking this position any longer will change a few things.

Understanding the following three principles will equip you with ways to think about what you want and allows you to deal with the kinds of conversations that are detrimental to your success.

Principle 1: Your Time Has Value

Some people are very demanding. They will stay on the phone even when you tell them you’re busy. They will send you emails when you ask them not to. They promise to meet you at three and won’t show up until four. These people waste your time. We often let people do this to us. 

As a founder, you can’t afford to any longer. You will have more important things on your mind. There is no time for tedious things, idle chatter, or talk about people who have nothing to contribute to your life. You will start noticing these conversations more and more as they become amplified by how much time they steal away from your life.

Every pointless interaction is another moment that could have been spent on thinking about value creation or customer delight.

Every dramatic story about meaningless events will take away from your precious time.

At that point, you need to start limiting access these people have to you. In some cases, cutting ties might be required. Don’t let others waste your time.

Principle 2: Your Vision Deserves Respect 

Some of your friends just won’t get it. They will complain that you prioritize work over them. For them, work is the annoying part of the day. They assume it is the same for you, and since you prefer work, they must be boring. And then they complain loudly, about how it used to be better in the past, and that the friendship must be meaningless to you. 

You will need to find people who respect that you have a vision. A friend will respect your choice to go on an adventure. They will respect you and your idea.

Find people who elevate you and enjoy talking about the bigger picture. Don’t let people pull you down and distract you from your goals. A friend supports your dreams when they see passion. Step away from people who caution you all the time and belittle your work. 

Principle 3: Like-Minded People Exist

You need to surround yourself with people who are compatible with your aspirations. Luckily, they are out there. Here is how to find them.

Seek out communities. There are plenty of communities for founders and indie hackers, both local and virtual. The IndieHackers community is particularly well-suited to find people from all over the world who are bootstrapping their own companies. Many questions have been asked, and many milestones were shared on that forum.

Find meetups in your area. Many bigger cities have regular IndieHackers meetups, but any startup-focussed meetup will attract like-minded entrepreneurs. And you can always start your own if you can’t find any.

Go to conferences. Among the most relevant conferences for bootstrappers are MicroConf and BoS. The communities you will find there are exquisite, and you will acquire loads of knowledge and build strong, often life-long connections with other founders.

Sharing your success will attract other successful people. Don’t be shy to share your successes, as small as they may be. People who are interested in other founders will find you. It is great to have a network of founders to be able to ask questions to.

In the bootstrapper scene, most of the people you will meed will have shared goals and shared visions. That will make it very easy to relate and connect. The only thing you need to do is to reach out.

When does this start happening?

The shift starts happening from the moment your idea gains traction. That can mean traction with a market or just traction with yourself. The moment you decide that you are a founder, things will change. The moment you start to really care, it will start.

This can be very early in the preparation phase of your business or when you start making some serious money. If you are passionate about building a business, it will happen eventually.

It ends when you want it to end. At some point, your business will create some level of income. You might have a few employees taking care of the company, so you don’t need to work on it full time anymore. At that point, you can retire and rake it in every month, or you can sell the business and rake it in all at once. 

At that point, the bootstrapped founder’s life-as-you-know-it is over. You may want to go again. Or you do something else entirely. That will be up to you.

But the open-minded and supportive friends you made along the way will stay with you for a long time.

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