Dennis Mortensen – One Signature Away From Riches but Wanted Just a Bit More

Dennis Mortensen is an expert in leveraging data to deliver business insights. A serial entrepreneur, Dennis built and successfully exited several companies before founding x.ai in 2014, a company that is solving a painful problem—scheduling meetings—through a sophisticated AI platform that saves people time and effort.

Dennis is a recognized leader, author, and university instructor in the field of digital data and analytics. Originally from Denmark, Dennis lives in New York with his family.

“Any startup is just the class of bad decisions. And the danger is that one of them might just be so bad that it kills the company. You just don’t know which one it is; you’ll know when it’s done.”

Dennis Mortensen

Worst investment ever

Dennis ventured into his first successful venture in 1996 when he started an internet company. He was the sole investor financing the startup on cashflow. He ran the startup for four years, and in 2000 he sold it for $11 million. At 27 years of age, $11 million was undoubtedly quite a kill.

Moving onto the next successful venture

Excited to have hit huge success with his first venture, Dennis took all the money he got from selling the company and invested it in another startup, a food delivery service this time around.

From his projections, this was going to be an excellent investment. So Dennis jumped in the deep end, money in both hands, and started to build up the team. Soon enough, the company was driving up revenue.

Doing things a bit different

Dennis decided that he would run his business model a bit different from other similar services. He charged slightly higher for the service; however, if the customer had any complaints about their orders, Dennis’s company would shoulder the blame and not the food vendors. Slowly but surely, this business model started eating up his cashflow and affecting revenue.

Pride comes before a fall

As fate would have it, Dennis got the opportunity to turn things around for his business. Another delivery service that grew to become the most prominent food delivery service company in the world approached Dennis with a merger proposal.

Dennis did his research and learned that indeed this would be a great merger. He got into negotiations with the company. The company offered him an 18% stake, but he negotiated to 23%. The company was adamant about offering him no more than 18%, which was still a staggering amount as Dennis would be the single biggest shareholder in that company.

In his delirious optimism, Dennis declined the offer and opted to keep running his business on his own. Three months later, this decision came to haunt him when he had to fold his business as he had no cash flow left. The delivery company he walked away from is now worth 10s of billions of dollars.

Lessons learned

You win some you lose some

Entrepreneurship is just a game you play to win, and sometimes you will lose. But there’s a game tomorrow as well. Don’t attach your life’s worth to the success of your company.

Don’t dwell on the losers

If you invest in a startup company or start a business and it doesn’t work, don’t dwell on it. Dust yourself up, learn from the loss, and move on to the next winner.

Andrew’s takeaways

Don’t make the wrong mistake

You can make many mistakes, but don’t make that one wrong mistake that’s going to kill your business.

Don’t be afraid to think differently

When you find an entrepre