Every Business is a Lifestyle Business

As we walked around the block, away from the team and the screens in the office, the founder started to open up:

“In the last year I’ve gained 20lbs, I’ve stopped exercising, I’m basically living at the office, not seeing my family, I’ve never been so stressed in my life.”

The t-shirt was definitely tighter and the bags under the eyes were definitely bigger than they were just a year earlier. 

Whether bootstrapped or funded, there is nothing easy about the lifestyle of building a business. Even those who appear to be on easy street, running cash generating machines, have experienced deep personal, and often existential, crises in achieving any modicum of success.

Steve Jobs once describe the entrepreneurial experience in stark terms:

I’m convinced that about half of what separates the successful entrepreneurs from the non-successful ones is pure perseverance. It is so hard. You put so much of your life into this thing. There are such rough moments in time that I think most people give up. I don’t blame them. Its really tough and it consumes your life. If you’ve got a family and you’re in the early days of a company, I can’t imagine how one could do it. It’s pretty much an eighteen-hour day job, seven days a week, for a while.Unless you have a lot of passion about this, you’re not going to survive. You’re going to give it up. So you’ve got to have an idea, or a problem, or a wrong that you want to right, that you’re passionate about. Otherwise, you’re not going to have the perseverance to stick it through. I think that’s half the battle right there.

As we walked and talked we started to unpack the sources of stress and anxiety this founder was feeling. They had taken on a sizable seed round to kick off their company. With that funding came expectations placed on themselves by themselves and by the promises they’d made to their investors.  And those promises added pressure. 

Pressure to move fast and break things, but now they were the thing that was being broken.

Pressure to grow the team to meet the next fundable milestones while the bank account shrinks and the milestones move.

Pressure to go big or go home, but not to that home. The home with their family. There was another, some other imaginary home that their sights were set on. While their real home was fading further and further away.

No investor asked this of the founder. But every investor asks this of the founders we fund.

Through our work with we’ve met hundreds of bootstrapped founders. Their reasons to start and scale a business are very similar to those running VC funded companies. But their pressures are very different from their VC backed counterparts. Many reject raising capital because it goes against the reasons they started their business to begin with.

For some, that reason was to the freedom to be their own boss. For some, it was to make more money than they could working for someone else. For others it was an unwillingness to compromise on their vision.

Yet, because they choose avoid VC funding they’re often marginalized as “lifestyle businesses”.

Contrast that with the lifestyle of the VC backed founder who reports to a board which governs what can and can’t be done. Or who pays themselves and their teams below market salaries in hopes that the value of their equity more than makes up for it (spoiler alert- the vast majority of the time it doesn’t). Or who finds themselves twisting and contorting their vision to map to the current waves of VC enthusiasm and the ever moving goal posts of fundable milestones.

Bootstrapping is not a panacea. And VC funding does not guarantee a ride on a rocketship. But starting a business does bring with it a certain set of lifestyle decisions.

Remember that the next time you’re looking down your nose at a “lifestyle business”. And chose your lifestyle business wisely.

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