Most entrepreneurs will tell you that starting their first company was one of the hardest things they have ever done. It takes countless hours of trial and error to find out what works. Often entrepreneurs experience a lot of failure before finding a winning formula.

We recently interviewed entrepreneurs from all over the world and asked them each to tell us some of the most important things that they wish they had known before they started their business.

Joshua Dziabiak, Founder of The Zebra

Comparing different car insurance companies to make sure you are getting the best deal can be time-consuming and confusing. That is where TheZebra.com, the latest startup from serial entrepreneur, Joshua Dziabiak comes to the rescue. TheZebra.com compares hundreds of insurance carriers to help you navigate hundreds of different plans and state regulations. Dziabiak says he wish he better understood the importance of budgeting.

“I’ve learned that the budget is more than just a financial indicator; it’s also a tool to drive specific business decisions and empower your team to make more informed decisions from a deeper understanding of the model. Center your team around a specific strategy and explicit goals — consider your impact versus effort and then align everything into a budget. Your team should sign-up for the budget, and it should be threaded into every decision you make,” says Dziabiak.

Jon Novak, Founder of Boomerang Transportation

After working for several years at one of the country's  largest transportation logistics companies, Jon Novak decided to branch out and start Boomerang Transportation. One of the biggest things that he wished he had understood before he started the company was that as the company's top manager, problems all funnel down to him.

“We have to wear many hats as the issues encountered vary greatly. From handling a specific accounting concern to fixing a broken door to communicating with an upset client, and dealing with personal employee troubles, we do it all. I wish I knew more of the breadth of problems that can occur in business, but the learning experience
is priceless. Much of what you learn on the job can even apply to other areas of your life,” says Novak.

Paul Dillon, Founder of Dillon Consulting Services

In 2011, Paul was asked by Crain’s Chicago Business to do research on how many local Chicago companies were actively hiring veterans. After completing this, he launched Dillon Consulting Services where he helps aspiring veterans who want to start their own business.

“The lessons that I wish I knew before starting my business were to be flexible and find an area or industry that is underserved where you can add value. Once you have done that, go for it. Don’t take no for an answer. If you are met with rejection, get up, brush yourself off, and try again. There is always more than one way to skin the proverbial cat,” says Paul. 

Roberta Perry, Founder of Scrubz Body

In 2005, Roberta Perry found that her skin was becoming dry, itchy and irritated. When she couldn’t find a product that completely satisfied her she decided to take things into her own hands. In 2006, with the help of her sister, she founded Scrubz Body.

"When I started, I wish I knew that marketing my products would encompass 90% of my time. I was all about the if I make it they will buy it mentality and then I could keep making more. Well, if no one knows about it, then what? And in this noisy world with thousands of other business vying for attention, if you don't reach the people who buy, you won't sell. And there goes the business," says Perry.

 Kristo Mägi, Co-Founder of Deekit 

Have you ever been on a conference call and wished you could be putting all your ideas onto a whiteboard for further discussions. Kristo Mägi and his company Deekit gives you the opportunity to do just that. With Deekit, your team can distribute ideas in real-time, no matter where members are located. When Mägi first started Deekit, he was just like anyone else starting a business—he wore the hat of many different positions. He soon found this to be exhausting but understood it took money to find other talented people.

“When I started, I knew we would face lots of challenges that don't contribute to core values. Like legal, taxes, bookkeeping, finance, etc. But what I didn’t expect is the real time it all takes. Sure, you can solve many of these things by outsourcing/using services, but it takes investments. When just starting you will count every dollar spent. And even then you have to take time e.g. to read through (so that you understand) legal documents before signing anything,” says Mägi. 

Greg Jakacki, Founder of Codility

Imagine trying to hire a computer programming without knowing what to look for. This is something that recruiters and hiring managers are tasked to do every day. Greg Jakacki and his company Codility are doing a great job of changing the way recruiting is done while saving companies money, time, and unneeded stress. Codility uses automated tools to assess the programming skills of potential candidates.

“One of the first challenges we encountered when we set up the company was how we handled our stock program — particularly restricted stock. One of our early employees was granted restricted stock and a large chunk of his holding was under vesting. His early departure from the company caused this chunk to turn into useless "deferred shares". This proved problematic because it did not enable the company to grant the reclaimed stock to somebody else. The forfeiture of unvested restricted stock should have automatically extended the options pool. I wish I had insisted on putting this mechanism in Codility's Articles of Association,” says Jakacki.

 

The Bottom Line

Entrepreneurs spend countless hours trying to build their companies. For anyone that has never started a business before there are going to be things that you will think back on later and wish you had done it differently. The abovementioned insights are important things to keep in mind throughout your entrepreneurial journey. 

Want to learn how to invest?

Get a free 10 week email series that will teach you how to start investing.

Delivered twice a week, straight to your inbox.