I Sold My Google-Backed Startup for $75 Million Yesterday–and I’m Scared to Death

My most recent startup, Smarterer, was just acquired by Pluralsight–and I’m genuinely scared to death.

It’s not because the acquisition isn’t 100 percent the right outcome. Combining the visions of Smarterer and Pluralsight makes our future nothing short of astronomical, and by being acquired we delivered an incredible financial return for Smarterer shareholders.

So, why am I so scared?

Because we are entering the incredibly complex, insanely demanding, highest-likelihood-of-failure, fourth trimester. It’s the stage of growing a company no one talks about–because in the startup journey, after an acquisition, many consider the story complete. Reporters focus their energy on the next rocketship, and investors go back to hunting other prey. Yet for the company acquired, the journey continues to unfold, and actually, the most challenging mile lies ahead.

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The 3 Decisions That Will Change Your Financial Life

There’s nothing worse than a rich person who’s chronically angry or unhappy. There’s really no excuse for it, yet I see this phenomenon every day. It results from an extremely unbalanced life, one with too much expectation and not enough appreciation for what’s there.

Without gratitude and appreciation for what you already have, you’ll never know true fulfillment. But how do you cultivate balance in life? What’s the point of achievement if your life has no balance?

For nearly four decades, I’ve had the privilege of coaching people from every walk of life, including some of the most powerful men and women on the planet. I’ve worked with presidents of the United States as well as owners of small businesses.

Across the board, I’ve found that virtually every moment people make three key decisions that dictate the quality of their lives.

If you make these decisions unconsciously, you’ll end up like majority of people who tend to be out of shape physically, exhausted emotionally and often financially stressed. But if you make these decisions consciously, you can literally change the course of your life today.

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5 Morning Rituals to Keep You Productive All Day Long

Here are five practical steps to incorporate into any morning routine to optimize your time at the office and maintain productivity all day long:

7 minutes of exercise. Yep, not 10 — just seven. Why? It’s short enough that it won’t impact the rest of your morning routine and long enough to shake off any residual sluggishness from the night before — including that extra glass of wine.

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The Big Lessons I Learned From My First Entrepreneurial Job

Instead of interviewing me, he pitched me on the opportunity: Running a College Pro franchise was a great way for college kids to learn to run their own business over the summer, painting houses and earning tons of money.

I remember my College Pro training fondly. There were PowerPoint presentations about the positive and negative qualities of oil and latex paints and role-playing exercises about pitching house-painting services and answering homeowner objections.

The training culminated in having to paint an actual house. It rained, however, and all I remember doing was eating pizza with the sales manager while he talked about paint-sprayer pricing.

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5 Skills You Must Acquire Before You Can Lead

How to Create Strategic Partnerships That Are a Win-Win

But it takes some skill and hard work to pull off being a leader.

Chances are, you’re already leading in some area of your life, even if not at work. Whether you love leading or feel reluctance in that role, here are five skills I’ve found essential for being the pathfinder in any area of your life:

1. Practice self-reflection.

One of the keys to being a good leader is having the ability to reflect back on decisions made and look at situations, whether good or bad, as lessons.

Once you’ve done so, you can actively apply what you’ve learned. Taking mistakes or failures in stride and moving forward is an essential part of becoming a leader of integrity. Many of these lessons are useful to share with staff and strategic partners. In my case, I’ve found they often apply even to my children.

2. Be proactive rather than reactive.

Successful leaders come to the table prepared for a variety of scenarios and know how to behave when situations fall apart or don’t go according to plan. Preparedness ensures that you’re never in a situation where you can’t offer value or assist in problem solving as needed.

This is simply being proactive. If you’re in a reactive state, chances are you’re not operating from a place of calm; your emotions are leading the charge. The best decisions, however, often result from when your thoughts and emotions work in tandem.

You must always consider not only what’s favorable for the company’s bottom line but also what’s best for the team and the overall morale of the company.

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9 Killer Tips for Building and Selling Your Business

Many Cinderella stories are about entrepreneurs reaching levels of success that even they themselves didn’t think possible. These are brave souls who built fascinating products, learned priceless lessons, and eventually sold their businesses in an inspiring way. Some took decades to reach their goals and others, to their own surprise, did it in a record time!

Gentry Underwood launched Mailbox App in January 2013. Finding that most people were tired of searching through lists of emails to find what they needed, he developed an app that simplified and streamlined the inbox. After a brilliant pre-launch video that went viral, he managed to created a virtual waiting list of users, who were eagerly awaiting their turn to download the app. He then sold his app to Dropbox for $100 million just 37 days after launch.

Everybody has a friend that at some point said something like, “I had the idea for Facebook. If only I had acted on it” or “That baby carrier was my idea all along”. The reality is, most ideas are not worth the paper they’re written on. The brilliance is usually in the execution of an idea and not in the idea itself.

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The Truth About Entrepreneurship

To most people, entrepreneurs are seen as one of two things: You’re either Mark Zuckerberg, wildly successful and famous, or you’re eating Ramen noodles and failing miserably at building a business, app, startup, etc.

You might disagree with that assessment because the only things being put on the front pages of media outlets (and I completely understand you’re reading this on a media outlet) are the stories of the Mark Zuckerbergs of the world. Or Richard Bransons. Or Elon Musks. Or Marissa Mayers. The list goes on.

Best selling author Chris Brogan said it best (and I’m paraphrasing):

“No one wants to see just your before pictures.” 

You know what before pictures are right? Those side-by-side comparison photos of people when they were extremely out of shape and then worked their asses off to get in amazing shape? Yeah, no one has ever wanted to just see the out of shape portion of that comparison photo. In fact, I’d be willing to bet people would turn away from just before photos.

On the flip side, people love after photos. How many fitness magazines are in existence right now? How many gorgeous celebrities have we seen on the covers of magazines, newspapers, TV, etc? How many successful entrepreneurs get featured on prominent news outlets for their successes?

The roller coaster ride that is entrepreneurship is barely talked about. Actually, that statement isn’t completely true. We know that entrepreneurs struggle (before photos), but only when there’s a success story to immediately follow (after photos).

The problem with the majority of entrepreneurship is that it sucks and no one wants to just read about the struggles, the constant ups and downs, the risks that don’t pay off, the tiny lessons learned and the small victories that keep entrepreneurs going. Unfortunately, people don’t realize that’s what happens when you work for yourself or start your own company. They’re only thinking about becoming “the next Instagram” or what their incredibly lucrative exit strategy is going look like.

The truth about being an entrepreneur is that it’s much harder work than showing up to a normal job and getting a paycheck every two weeks.

The truth about being an entrepreneur is that something like 90% of people fail within the first few months and completely give up (missing an opportunity that might be right around the corner from failure).

The truth about being an entrepreneur is that there are rarely successful exits, especially ones of the billion dollar variety.

The truth about being an entrepreneur is that barely anyone will want to see or talk about your struggles and early phases. There’s a slim chance your idea could get some attention, but it’s highly unlikely unless you have credibility or existing connections.

The truth about being an entrepreneur is that it’s downright hard and lots of people are going to doubt you along the way.

But you shouldn’t let those truths discourage you.

Use those truths as motivation to understand the world of entrepreneurship; whether you’re starting your own company, building your own business or creating something unique.

There will always be exceptions to the rule, but there will never be another Mark Zuckerberg or Instagram. Strive to carve out your own path and know that it’s not going to be an easy road but that you control your own future.


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