The Biggest Challenge Entrepreneurs Face

The Biggest Challenge Entrepreneurs Face

The Biggest Challenge Entrepreneurs Face


Alan: Running a company is never easy and you know, this show at American Dreams talks about pathways in life. And I had a guest come on once and say “In life there is no path, but it’s really the path is created by the series of choices that we make and the consequences that follow.” And so I wanna step back into the mind of the entrepreneur specifically when you stepped in and became part of insynctive, you know, there was a transition that that involved. From the founder and you taking the reigns as the CEO, but in the process of scaling a company, what are some of the biggest challenges that the entrepreneur faces?

Gary: Well, I look at it as it’s not a straight line to success. And that success or nonsuccess is determined by the quality and number of people you have surrounding yourself. And having been in this business, that was one of the components that was really key and critical for me in order to take on this opportunity with the entrepreneur. And having the mindset of putting together a series of milestones that achieve your goal is what’s critical so that you have measurable results that you need to achieve. And every time you hit those results, you know you’re on track to get to where you need to go. And one of the things I’ve learned in the past is that you’ve got to get the company to break even in order to have a real company.

Alan: You know; I like that measurable goals for building accountability into that.

Gary: Right.

Alan: When you find that you’re not meeting goals, typically, how do you step back and re-evaluate?

Gary: Well, part of being a leader you have to surround yourself with people who have their own opinions. Many of the time they are gonna have a diverse opinion then you do. And so if you’re not on track to meet your goal, you have to reevaluate. You have to take in to consideration what the clients’ needs are, what the distributors’ needs are, what your employees are suggesting, what your network of advisors are suggesting, and then you come together and you put together a new path. And ultimately, it’s always a bunch of checks and balances along the way.

Alan: So what keeps you motivated to drive the company?

Gary: Well, you know, it’s exciting to build something, it’s exciting to see that it’s actually working. And it’s exciting to see that it’s actually helping people do things better, faster, and more efficiently, more effectively. It’s great to see us being compared against some of the other groups out there that have raised, you know, hundreds of millions of dollars.

Alan: Okay, so when you are thinking about how you’ve come so far, are there any lessons that you’ve learned or experiences you can look back on and say, “you know that was a great experience in my life”?

Gary: Yeah! Even the ones that aren’t such great experiences add up to the sum and total. At the end of the day, as you mentioned, we are a sum of all of our experiences, both good and bad. And you have to take both into consideration to help motivate you as an entrepreneur. Cause there’s a lot of days, there’s a lot of nights where you’re making decisions you’re taking everything in to consideration, but at the end of the day, it’s your decision. And you know, we either win or lose on those decisions. By having more experience, you have the ability to make better decisions along the way.


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Alan Olsen, CPA

Alan Olsen, is the Host of the American Dreams Show and the Managing Partner of  GROCO is a premier family office and tax advisory firm located in the San Francisco Bay area serving clients all over the world.

Alan L. Olsen, CPA, Wikipedia Bio is a proud sponsor of The American Dreams Show.



The American Dreams show was the brainchild of Alan Olsen, CPA, MBA. It was originally created to fill a specific need; often inexperienced entrepreneurs lacked basic information about raising capital and how to successfully start a business.

Alan sincerely wanted to respond to the many requests from aspiring entrepreneurs asking for the information and introductions they needed. But he had to find a way to help in which his venture capital clients and friends would not mind.

The American Dreams show became the solution, first as a radio show and now with YouTube videos as well. Always respectful of interview guest’s time, he’s able to give access to individuals information and inspiration previously inaccessible to the first-time entrepreneurs who need it most.

They can listen to venture capitalists and successful business people explain first-hand, how they got to where they are, how to start a company, how to overcome challenges, how they see the future evolving, opportunities, work-life balance and so much more..

American Dreams discusses many topics from some of the world’s most successful individuals about their secrets to life’s success. Topics from guest have included:

Creating purpose in life / Building a foundation for their life / Solving problems / Finding fulfillment through philanthropy and service / Becoming self-reliant / Enhancing effective leadership / Balancing family and work…

Untitled_Artwork copy 4 (Also sponsored by GROCO) provides free access to content and world-class entrepreneurs, influencers and thought leaders’ personal success stories. To help you find your path in life to true, sustainable success & happiness.  It’s mission statement:

In an increasingly complex and difficult world, we hope to help you find your personal path in life and build a strong foundation by learning how others found success and happiness. True and sustainable success and happiness are different for each one of us but possible, often despite significant challenges.

Our mission at is to provide resources and firsthand accounts of how others found their paths in life, so you can do the same.

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