Our Top 5 Episodes from Season 1

As we prepare for Season 2, we paused to take a look back on the top episodes over the past several months.



[5] The First 30 Days of Starting a Company – Advice from the Pros

Kevin O'Leary

We’ve talked about the mental preparation required to become an entrepreneur and the financial considerations you’ll want to make before starting a company.  Today, we want to touch on some of the critical areas you’ll need to focus on in the first 30 days of starting your new business.

This is a time when you’ll be making major decisions, which can be thrilling but also intimidating. How do you know what decisions to make?  What to focus on?  If your product or service will be successful?

To get some expert advice, we asked a number of successful entrepreneurs and investors about their views on the most important things an entrepreneur should tackle in the first 30 days. Ryan Allis, Rand Fishkin and Kevin O’Leary underscored the importance of the careful balance between action and reflection — of going out in the world and testing your ideas, but also taking the time to step back, sift through the data and make sense of it all.
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[4] Guest Post: 2 Months after walking away from A.T. Kearney

Businessman chained to a large ball

Over the past two years, I have had the opportunity to travel the country, work with Fortune 1000 executive leadership, and tackle the most complex problems in business. In 2015, I was inducted into A.T. Kearney’s fast-tracker program as a result of where I fell among the top 100 of my colleagues worldwide. With a promotion staring me right in the face, I decided to walk away from a consulting career to pursue my dream of becoming an entrepreneur.

My family, friends, and colleagues continue to ask me, “Aren’t you scared? What if it doesn’t work out? Where did you find the confidence to take this leap?”

It all started three years ago. I was part of a leadership development program that wasn’t challenging and in a personal relationship that wasn’t healthy, all while feeling stuck because my employer was paying my tuition expenses to obtain my MBA at Boston University. I was supposed to feel fulfilled, but I was completely unsatisfied and to make matters worse I had no idea what to do about it.

Businessman chained to a large ball

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[3] What’s your number?

Budget calculation

Most execepreneurs often jump straight to considering the financial investment required to make the leap without properly considering the personal aspects of it.  That’s why we spent time on the mental aspects first.

Of course, it’s hardly surprising that we spend a lot of time on the financial side. Cash flow is a fickle thing for small businesses, so you want to make sure that you’re prepared to get through the first few years intact. This is especially the case if, like many of us, you want to do your best to insulate your family from the volatility of a new venture.  As Mike Tayter said in Episode 1, you don’t want the cash flow to make the decisions for you.

Your “number” is the amount you need to bank before you feel comfortable leaving your corporate role. It’s based largely on your lifestyle expenses and the cost of starting and initially running your business, plus a couple of variables unique to your situation. While everyone’s number is different, the key components are largely the same.

Let’s go through the step-by-step considerations I made when putting together my own plan.


Before you get going, I suggest that you consider three key issues: your lifestyle, your runway, and your buffer.

First, how willing are you to sacrifice lifestyle? I know that a lot of execepreneurs, myself included, didn’t want their families to experience too radical a lifestyle shift during the transition. It was also very difficult to determine where to cut. We had quite a bit of fixed costs that would take a lot of work to change (mortgage, childcare, etc.). You need to think about where and how much you are willing to cut and use that in your calculations.

The second factor is the amount of time you want to give yourself to “make it.”  I wanted to have our life fully funded for at least two years, and a lot of my peers put a similar timespan on their own ventures. Realistically speaking, I believe that real breakthroughs need more time to take hold — on the order of three to five years — but saving that amount of money can be daunting for most people. [Read more…]

[2] 4 Ways Entrepreneurship is Harder than being an Executive

Execepreneur lost as he leaves corporate and becomes an entrepreneur

When I was doing my MBA, I took a class with Harry Kraemer, the former CEO of Baxter International. One of our assignments was a short essay on where we wanted to be in ten years, and for some wild reason I said that I wanted to be one step away from the C-Suite at a Fortune 500 company.

He wrote six words on my paper: “Is that really what you want?”

Given our interactions, he had gotten insight into something that took me a few more years to figure out. He knew that while I might have enjoyed the recognition and influence that comes with a senior job at a big firm, I would probably detest the role itself — not to mention everything required to get there.

But that, of course, doesn’t mean it’s easy to walk away. There are a lot of great perks that come with senior management jobs: the pay, the top-tier team, the stability, the infrastructure, the recognition, and of course, business class travel.

On the other hand, being an entrepreneur is a lot less romantic than culture and the media make it out to be. It’s incredibly difficult to be an execepreneur.

The question is, are you ready for the realities?

Reality #1: You will miss the cash flow [Read more…]