Category Archives: Entrepreneurship

Leaving the startup I founded 9 years ago

The Beat The GMAT Team

Today is my last day at the startup I created.

Nine years ago this month, I was in my dorm room at Stanford with a laptop on my lap and a credit card in my hand. I was about to make a $4 purchase for a domain name that would change my life: beatthegmat.com.

At the time, I had no intention of building Beat The GMAT into a business. All I wanted to do was blog about my experiences studying for the GMAT test as a broke college student.

That blog would later turn into a discussion forum, then a niche MBA news network, then an online community, then a social media platform, then a recruiting platform for MBA service companies and MBA institutions, then a highly profitable bootstrapped business, then an acquisition by an incredible education company.

It was the best $4 I’ve ever spent.

When I told friends this week that I would be leaving my startup after 9 years, they asked whether it is a bittersweet feeling. It doesn’t feel bittersweet at all. The business, the community, and our clients are all in great shape. It was simply time for me to let go and move on.

Rather, the primary feeling I have right now is gratitude.

I’m grateful to have worked on a project with a deep social stewardship mission, helping millions of people achieve their dreams with higher education;

I’m grateful to have collaborated with amazing team members who sacrificed blood (literally), sweat, and tears to make this venture succeed;

I’m grateful that Beat The GMAT could find a home with such an amazing parent company, who has done so much to further invest in the growth and potential of my startup;

And, I’m most grateful that I could share this journey with my wife, who quit her job and joined my startup right after our honeymoon.

Now that I am at the end of the road, I find myself reflecting a lot on Beat The GMAT’s long history. Here are a few moments that come to mind:

Continue reading

Elon Musk

“Being an entrepreneur is like eating glass and staring into the abyss of death.”

— Elon Musk

Amen, brother.

Should you do a startup with your spouse?

Spouse Founders

DON’T DO IT.

That’s my initial gut reaction whenever someone asks me whether it’s wise to work with a spouse or family member.

My wife and I have been running our startup together for the past five years; don’t get me wrong, we love it! We enjoy the challenge of building a business together and appreciate the unique value that each of us brings to our work. Our work life is a huge source of joy in our marriage.

But here’s the truth: you can truly love someone as a person, but still be incompatible with him or her as a professional.

Not being able to work with someone you love says absolutely nothing about the strength of your relationship to that person. Personal complementarity does not correlate directly with professional complementarity. When conflicts arise with your spouse in a professional setting, you risk having those issues bleed into your personal life as well. For that reason, I believe that it’s generally too risky to work with a loved one because the cost of failure could be the failure of your relationship (how much is that worth to you?).

Nevertheless, if you still want to see whether you and your spouse can make it as a startup team, consider the following scenarios to test your professional complementarity.

Continue reading

I lost so much money from this stupid startup decision

Shut Up And Take My Money

tl;dr: If you are a startup founder who wants an acquisition, then you probably want to form your company as a C-Corp. This might save you a crazy amount of money on federal and state taxes due to Qualified Small Business Stock.

There are very few things that I regret about how I ran my last startup, Beat The GMAT: my team bootstrapped a highly profitable business over multiple years; built a product that helped millions of people achieve their higher education dreams; and fostered a team culture that was close-knit and fun.

But I do have one serious regret: forming my company as an Limited Liability Company (LLC) instead of a C Corporation (C-Corp).

This little business decision cost me a ton of money when my company got acquired. The reason why: Qualified Small Business Stock (QSBS).

Continue reading