Recently, my son spray painted our driveway, tagging the cement like a wanna be entrepreneurial gangsta. My wife was furious. I laughed, and now I smile each time I pull into the driveway and catch a glimpse at this horrible attempt at driveway beautification. 

Hours before, my son had presented an elaborate business plan for which he required financial backing. For a small investment, approximately $20.00, he would purchase both white and black spray paint, and number stencils. He would market his services to neighbors seeking to place proper house identification numbers on the curb at the base of the driveway. He had recognized this subtle, yet elegant method by which a house could be identified in other neighborhoods and believed ours was ripe for the transformation. 

Upon completion of the presentation, I asked a few softball questions and within minutes we were on our way to the local Home Depot to secure the necessary supplies. Rather than taking an equity stake, I decided upon a small loan so that, upon payback, he would not be diluting his ownership and be free to keep all profits.

Prior to embarking on his new venture, I encouraged him to test the process on our house at which point he could take photos for marketing purposes. My son never approached a single house. The loan is now in default and arrangements are being discussed. He has told me it’s just a temporary setback. 

When I was 8, my first business was that of a shoe shine boy. I was shagging golf balls for a local golf course during a 3-day tournament, and I spent the entire day in the woods on a nasty dog-leg right. When the weekend warriors would inevitably slice into the woods, other boys and I would run along, scoop up the lost golf balls and return them for a few tip dollars. On this particular day, it was rainy and cold and I was downright miserable. The ‘go fetch’ business model seemed ridiculous to me. 

Later that afternoon upon entering the clubhouse, I recognized that each and every golfer had shoes covered in grass clippings and mud. The light bulb went off, and I immediately started walking through the locker room peddling an overnight shoe shine business. Of course, I had no shoe shine supplies, but figured I could hit the store before it closed and work through the night if I had to. I remember that night like it was yesterday, and I ended up shining around 30 pairs of shoes at $3.00 a pop. Of course, this was a strategic price since my hope was that each man, upon satisfaction with the service, would just slip me a five. The next morning I raked in over $150 and proceeded to follow the same model the entire weekend, never stepping foot in the woods again. I secured that business each year for the next several without any of my cousins (the other grunt workers for the tournament) knowing just how profitable the enterprise was. They always laughed when they left for the night and knew that my job was just beginning. I always had the last laugh.

Shortly after Mark Cuban sold Broadcast.com to Yahoo for a billion dollars in stock and subsequently hedged the entire position at the peak of the dot com market, he started his blog which I devoured daily. I was beginning my investment business and sent him an email asking whether he had any advice. He simply replied “Work Hard, Work Smart.” I’ll never forget this and will thank him in person one day.

Throughout my life, I have tried to see around the bend and use speed to my advantage. After failing miserably with a tech startup in the late 90s, I became a stock broker for a year. Our sales’ cycle was built around getting folks to a seminar where we hawked our products comprised mostly of loaded mutual funds and annuities. It wasn’t for me. As soon as I could, I jumped ship. It didn’t make sense to me that anyone would pay a commission for something when there were folks charging a flat fee to do the same thing. I resolved to become a fee-only adviser and if it didn’t work, I decided the business just wasn’t for me. I was told by countless people that I would fail. Today, our firm works with hundreds of families throughout the United States. 

A year or so ago, I felt a strong desire to help more people understand the world of budgeting and personal finance. Sure, there are other folks out there who’ve been speaking truth on this subject for a long time, but I’ve never personally identified with them.  I have spent the last decade developing methods that I’ve used for my own finances that I felt others might find helpful. DIY Money was born, and through a lot of hard work and smart moves, the podcast is currently one of the fastest growing financial programs on the interwebs. We seem to be helping folks; that means we’re doing something right.

Life is too short and this world is too vast for one to be miserable. I smile at the spray painted numbers at the base of my driveway because I want my son to think of creative and new ways to pursue serving others. I want to encourage this entrepreneurial drive and not stifle it. I want him to always know that, regardless of what happens in the world, creative people who are solving problems will always be in demand. 

I believe that all of us have a desire, a dream and a goal to achieve more. If you find yourself in a rut, looking for something new, may I encourage you to look around, look closely at the problems you face each and every day and work like crazy to figure out how to solve them. May you never give up on life, may you never stay down when you fail, and may you never stop looking to help others. 

I sat down to write a piece about how to become an entrepreneur and realize that it morphed into something of a personal bio. Maybe someone out there just needed to hear this today. 

Thank you for giving me a platform to share.