4 Smart Things That Would Have Changed My Small Business Life

Running a business was exciting at first. I felt the freedom of controlling my own destiny while working with my closest friends, daydreaming about the next big breakthrough and planning for the day that financial freedom would finally arrive.

Unfortunately, I wasn’t prepared for the constant state of struggle and hardship that lay ahead. And as I look back on those years, I wonder if they would have been easier had I known then the four smart things I know now.

1. Perseverance and dedication will get you through the down times.

While slogging your way through the trenches of the typical small business, you’ll sometimes feel that it’s time to throw in the towel. But perseverance and dedication will get you through those dark times. When you’re in those trenches, do what you have to, to keep your business running during the day, and spend your nights working to making it better.

A few short weeks after joining Infusionsoft, my excitement morphed into a steady stream of negative emotions: struggle, disappointment and the fear of business failure. For three years, I never felt that things were going to be fine. Checks that came in were already allocated to expenses, which meant there was little or nothing to take home. The disappointment on the faces of the ones I loved and the feeling of not being able to provide for them better was demoralizing.

Like many struggling small business owners, I felt trapped. Sure, I was passionate about the work. I believed that the business would be successful, when so many believed otherwise. And there were times when my wife wanted me to leave it all behind, put my degrees to work and provide for and spend more time with my family. But even if I had wanted to leave my co-founders, that would have been difficult. We had put everything into the business, having signed an office lease, racked up credit card debt and signed personal guarantees to secure a line of credit.

So, I continued to persevere: I spent days trading hours for money and nights burning the midnight oil, shaping our business’ future. I had to employ mindset strategies in order to stay balanced and refuel when I was out of steam. Eventually, though, we were able to automate our follow-up, which helped us grow sales and save time. I credit the perseverance and dedication I put into the business at its start for helping to elevate it beyond those initial three dark years of its existence.

2. Family comes first, except when business comes first.

You can bring friends and family into the business by setting up boundaries around their employment, but if things still don’t go well, people don’t believe you’ll actually let them go. Should that day arrive, however, the relationship will be ripped apart, and there’s nothing you can do to build it back up. You’ll have to wait until those individuals forgive you, and that can take time and many lonely days, not to mention awkward extended-family gatherings. It can be hard to forgive an ex-boss if you’re the one let ago, and you’re still upset and struggling to replace the lost income.

In the early custom-software days, a client that constituted 65 percent of Infusionsoft’s revenue decided to outsource his work to India. In the blink of an eye, our business suffered a blow that almost killed it. I couldn’t make the numbers work to justify keeping one of the partners, despite cutting expenses, giving up a paycheck myself and relying on credit cards to put food on the table. We had to let him go.

I spent nights and weekends trying to figure out a way around this decision. There were arguments, hurt feelings and frustrations until I realized that the business had to come first if it was going to survive. The next day, I met with the partner and said goodbye to a friend. Firing friends or family members is hard.

3. Trust your gut.

You can collect all of the data and wisdom this world has to offer, but at the end of the day you need to trust your gut. Your gut instinct is a result of the years of experience that you have, combined with your natural innate responses to certain situations. You have this instinct for a reason and should probably rely on it more than you do.

Every decision I’ve regretted started with ignoring my gut instinct. In 2009, for instance, this mistake resulted in the highest churn rate in our company’s history: The problem: After listening to advisors and running a test to remove the setup-and-training fee we normally charged, I gave the go-ahead to eliminate it.

Sure enough, removing the setup fee prompted an influx of new customers. Unfortunately, a large number of customers were also frustrated and confused as they sought support that was no longer offered. Our churn rate skyrocketed. Eventually, we realized that this business model wasn’t going to scale to the masses. In fact, we were doing a disservice to customers by providing a tool to grow their businesses without the help they needed to use it.

Instead of listening to my gut, then, I had relied on experts and data to paint the picture that would allow me to sleep at night.

Yet, in fact, I traded one sleepless night for another and learned that paying attention to my instincts was instrumental to key decision-making. Today, I still pay attention to smart advisors, but I don’t let them override my gut.

4. You will get stronger.

You can overcome any barrier once you’ve experienced the dark shadows of owning a small business. The lessons that you learn and the character you build aren’t taught in a classroom or in corporate training. You build a boot-strapping mentality and an iron stomach that can handle any acid that comes your way. The trials you face daily only strengthen the belief that you’ll accomplish big things.

The three darkest years of our company’s history created the empathy that I now have for small business owners. I used to say I wouldn’t wish those trying times on my worst enemy, but I probably used that phrase for dramatic effect to underscore our own experience.

Indeed, I may have had competitors in mind when I said that, but I the reality is, I hope they never go through what we did, because that’s what created the fire, drive and commitment in us to change the world one small business at a time.


Isler Northwest LLC is a firm of certified public accountants and business advisors based in Portland, Oregon. Our local, regional, and global resources, our expertise, and our emphasis on innovative solutions and continuity create value for our clients. Our service goal at Isler NW is to earn our clients’ trust in us as their primary business and financial advisors.

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