A Five-Step Program for Middle-Aged Entrepreneurs

If I were an aspiring entrepreneur, I would take a vacation from my day job during Relationship & Information Series for Entrepreneurs (RISE) week and attend as many sessions as I could. This year, I was happy to do my part and present on Austin Ventures fundraising Monday, May 13, as well as Tuesday, May 14, with panelists from the Central Texas Angel Network.

The spirit of this post is as a RISE talk that I could have given, but didn’t.174245676

Bill Wood, founder of Silverton Partners, said something at the ATC CEO Summit the week before that got me thinking about teams of founders. The majority are in their 20s, Wood said. The good thing is that they don’t know what’s not possible. Perhaps half of the RISE attendees I’ve seen fit the young-founder profile with drive and ambition. But a large percentage I would classify as middle-aged entrepreneurs.

I started to think about the advice I would give them.

So, middle-aged entrepreneurs, here it is: my take on your five-step program to entrepreneurial freedom.

Step One: You need to shrug off the big-company attitude. When you are a big-company executive, people pay attention to you because you have the resources of a big company. At a startup, don’t expect that type of treatment from anyone. Start by reading Man’s Search for Meaning by Viktor Frankl to get centered and find your inner passion.

Step Two: You need to learn how you’ve been manipulated. One of my favorite books to this end is Influence: Science and Practice by Robert Cialdini. This is important because it will put you in tune with human behavior. The book is also full of very practical early-stage marketing advice so you can break through the noise.

Step Three: You need to think big or you will fall into the pattern of being a first-stage entrepreneur. If you become a first-stage entrepreneur, you will very likely never have financial freedom. The best book on how to think big is The Innovator’s Dilemma by Clayton M. Christensen.

Step Four: Read my Lucky7 post on the seven lessons learned on the journey from founder to CEO. It is written by a middle-aged entrepreneur. I’m dedicated to writing many of my lessons learned over the course of founding five businesses on the Wharton Blog Network and on Lucky7, which is a tribute to my mom. To get you started, here are two Lucky7 posts on winning your first clients (post one and post two), along with a third on how to build your team. I also suggest reading The Bootstrapper’s Bible by Seth Godin (available free here) and The Art of the Start by Guy Kawasaki.

Step Five: Have the humility and self-awareness to surround yourself with great mentors, from your angel investors, to your advisory board, to your board of directors, to your CEO or executive coach. You are really going to need them.

Good luck.

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