What I Learned About Entrepreneurship From A Downtrodden Lyft Driver

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light your entrepreneurial fireDuring one of my frequent Lyft (BTW – I love Lyft – if you are only an Uber user, here is $10 towards Lyft – it’s cheaper) rides back home from the airport, I had a really chatty driver. And, honestly, I kind of love chatty drivers. I get to see a completely view of things.

I started asking the usual things that I ask in order to start a conversation – why do you drive for Lyft, do you like it, etc. As we started talking, he asked what I do and I told about my work as an entrepreneur and consultant. He told me that he had tried his hand at online marketing and eBay sales, but remarked that there was always someone out there who is screwing you, or cheating you, or out to kill your business. He then told a story about his buddy that was selling on eBay and Amazon. This friend, he said, got “too successful”, so naturally eBay and Amazon wanted to shut them down. We talked for a few minutes about the business model of eBay and Amazon and how shutting down successful sellers didn’t make any sense to eBay or Amazon financially. He wasn’t totally buying my reasoning, but we continued chatting.

As we did, what I heard in his voice, more than anything, was frustration and desperation. So, I asked him if there was any way that I could help, and that I have been successfully doing online marketing and helping startups for 20 years. There is probably something that I could help him understand or get better at while we sat in traffic on Rte. 93. He rattled off a bunch of ideas that he had, and I talked him through multiple scenarios on how he could leverage only his time and effort to grow these ideas into a relatively stable income stream. At every turn, he said that he had “already tried that” or “been down that road, chief” and he was convinced that “the system” was rigged against him. And on top of that, he had 3 kids and a wife who didn’t work. They were holding him back.

“I have a wife and three kids – that holds me back – A LOT. And my wife doesn’t have a job…”

I was stunned when I heard this – my jaw literally dropped. Immediately, I challenged him with my own stories of having a young family and starting something, or taking a risk joining someone else’s start up. After a few more miles of cajoling him, I think I had pushed him too far. I told him that my 5 kids were the reason why was getting home after 10pm after my 6th multi-day trip in as many weeks. My 5 kids were the reason that I was up before the sun working with as many clients as I possibly could. My kids are the reason that I start startups and help companies grow. My kids motivate me to do and be more so that I can show them that they can do and be more. My wife doesn’t have a traditional job either – she is the powerhouse behind JuliaCooks.com , a Boston-based baking and personal chef service (and if you live near Boston, try her Award Winning Apple Pie – it is amazing, and it will likely be delivered to you by yours truly). She has created that business to not only create economic agency for herself, but to satisfy her desire to share and express herself through her food.

But my poor driver couldn’t be inspired enough. By the end of our time together, he was still convinced that the world was against him. This was disappointing to me, I thought I might get his entrepreneurial embers going again. I thought that he might end his year with a renewed vigor about making his situation better.

As I sat in silence towards the end of my ride, I thought about the work that I do with companies and startups and entrepreneurs – I help them refine their messages and processes so that they can share their brilliance and build businesses that can sustain them and their employees. I can teach them about marketing acquisition and customer value economics and how to document and refine their processes so that they can do better work more efficiently. But what I can’t do is create the fearlessness or attitude to know that you can create a business. I can help you drive forward, and I can help remove the obstacles that you put in front of yourself, but I can’t hit the start button. Unknowingly, my driver gave me a valuable lesson that I think about as I work with my clients today. Optimism about your ability to make a difference for yourself isn’t rational. Optimism isn’t the result of careful business analysis. Optimism is as crucial an ingredient in the entrepreneurial fire as oxygen is to the campfire. Businesses die without the power of optimism.

My witty, pop-culture maven Lyft driver has the tools to create a business to change his circumstances – in fact almost anyone has those tools innately – but he didn’t give himself permission to keep his entrepreneurial spark alive. He let everyday circumstances become immovable obstacles. He used his position of responsibility as a husband and father to shackle himself to the menial tedium of being ordinary. This guy had creativity and insight – he was anything but ordinary. However, his drivetrain of optimism was decoupled. He perceived of himself as oppressed, and he chose to, like “the mass of men (to) lead lives of quiet desperation”. (That is from Thoreau’s Walden – here is an Amazon link – it is worth a read or a re-read.)

It is so crucial that anyone who has the entrepreneurial mandate to follow it wherever it may lead them. In today’s world, entry level and mid-career jobs often don’t pay enough to allow you to afford working for someone else exclusively. You have the brilliance to create something of value or have the skill to offer a service that someone will pay for – you just have to find it in yourself – it is there. If you are like my downtrodden Lyft driver, or like I was after the dotcom crash a million years ago, not making enough money and responsible for a family, you are faced with choices. You can draw on the power of your own optimism and create a path of independence and success for your children to witness, or you can lump yourselves in with the quietly desperate masses.

It is your obligation to make try and make your mark, and not just for yourself, but for those that depend on you. It is your obligation to nurture the spark of optimistic entrepreneurship within yourself so that you can create a burning torch for your children to see and follow. You can carry this flame forward on your own terms, like my wife and I do, or you can make your own entrepreneurial path within another organization. Your own internal engine of optimism and confidence in creating positive change can burn brightly in any environment. If is your responsibility to unshackle yourself from desperation.

My mission is to create a wonderful, satisfying life for my family on our own terms. For my wife and I, that means creating our own versions of sustainable business. For you, it may be driving for Lyft while you are your way somewhere else, it could be creating a mammoth business with thousands of employees, it could be taking on a new role at your current company or it could be making a few dollars here and there through some activity that stirs the passions of your soul. My sustainable business is about helping you create your sustainable business. My job is to help your business grow into a tree that provides you with sustenance, emotionally and financially. Let me know how I can help. And so that you can see that I get it – I understand what you are going through – here is a long-ago post about the perils of entrepreneurship when you have a family – 7½ Reasons To NOT Start A Company – read all the way to the end – it will be worth your while.

Good luck – and I gave my Lyft driver a 500% tip. I hope that gave him enough breathing room to add oxygen to his fire. If you need a boost in either starting your own business or scaling a business you have check out #TRIPLETHIS for Startups & Entrepreneurs.

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