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The Future Is Now: “Instead of waiting on a platform, you could be sitting at a coffee shop and alerted when the train is coming” With Greg Shepard

…a cloud-based technology that leverages data from riders to learn patterns and to let people know when trains or buses are arriving. This means that instead of waiting on a platform, you could be sitting at a coffee shop and alerted when the train is coming — all through a tiny chip. The data this technology provides […]


…a cloud-based technology that leverages data from riders to learn patterns and to let people know when trains or buses are arriving. This means that instead of waiting on a platform, you could be sitting at a coffee shop and alerted when the train is coming — all through a tiny chip. The data this technology provides allow transit providers to make bus routes more efficient, will let people know how far apart buses are, and limit how many unnecessary vehicles are on the road. Frankly, not everyone can afford Uber. Through this technology, not only is the user experience for a commuter improved, but we are empowering people from all socioeconomic situations the ability to move freely — regardless of income.


I had the pleasure of interviewing Greg Shepard, a private angel investor, VC committed to building and running sustainable growth businesses. His former company, AffiliateTraction, was acquired by eBay Enterprise Marketing Solutions in January 2016 as a part of a $985M deal. The deal also included the purchase of AdAssured, another company founded by Greg. This transaction won four silicon valley PE awards from M&A Advisor. All included a curve out of 14 companies followed by exiting 12 and buying three, two of which were Greg’s. Greg’s book ‘Meet the BOSS — The Agile Playbook for Startups’ and TEDX talk is slated to be published in 2019 Read more about his M&A Advisor wins here.


Thank you so much fo joining us Greg! What brought you to this specific career path?

Ever since a young age, I’ve had the determination to do things that had not been done before. When you work for someone else, you’re working to replicate a vision or product that has already been done — which means you don’t have the space to pursue the change you want to, you can only “improve” not “create.” Only until you take the leap to be your own boss are you able to truly implement change — done in the way you know would be most effective.

I recognized early on that many companies were using inefficient, old-school methods that set them back — and were subsequently unwilling to change how they operated. Changing the environment around me for good is a part of my DNA, both professionally and personally. From that lens, doing anything else but being an entrepreneur felt like a forcing a round peg into a square hole.

Instead of a primary focus on company creation, today my passion has pivoted towards giving guidance to entrepreneurs I believe in to succeed. I can do more good by helping people scale than I can by creating on my own companies. This is a core value and lesson that my upcoming book ‘Meet the BOSS’ covers.

Can you share the most interesting story that happened to you since you began your career?

When I first started my career, I had interviewed with a company for six months before convincing the CEO to hire me. During that time, in order to keep myself afloat, I was working nights as a security guard, delivering newspapers in the early morning and waiting tables when I wasn’t at work. I remember I had two suits, two ties and two pairs of socks that I had purchased at Goodwill that I would rewash.

One day, after months of working to provide value for the brand, a mentor pulled me aside and asked why I had only two suits — and then saw that I had a picture of a Ferrari on my desk. I’ll never forget that day, he took me to a Ferrari dealer, bought himself a car, and let me drive it off the lot to valet for lunch. Then we went and bought some suits. He recognized my determination and drive to change the world around me for good, and used his influence to build me up.

The moral of this anecdote is to not only share every day, arduous challenges I overcame in the beginning, as many entrepreneurs encounter obstacles when starting out. The value here is to show that not all company leaders look out for their employees like my mentor had, at least not without you earning it — you must give before you take.

So many brands tout their commitment to diversity and how innovation is at the core of their DNA. But once you look under the hood — you see they’ve lost their way. The reason technology inspires me is that tech companies have transformed almost every industry.

It’s the one game changer that has single-handedly leveled the playing field. From the rampant criticism that Tesla faced, to Apple who fought for survival from Day One, to an early Jeff Bezos when monster retailers laughed at him — these entrepreneurs have proved that technology does have the ability to change lives for good. Today we come full circle with a SpaceX rocket to Mars in the works. Like a raindrop causing ripples across a still pond, tech disruption has become commonplace, causing entire ecosystems to transform.

Within my consulting work, I think of myself sitting in that cubicle looking at that printed photo of a Ferrari, and I remember how lucky I had been to have mentors not only in business but in ethics that taught me the value of personal integrity.

I recognize the value of building up people around me that fill my weaknesses and help me hold steadfast to my values. My passion is being able to give entrepreneurs the knowledge they need. Which is defined as obtaining wealth through exits, and subsequently spreading the liquid flow of wealth to the world. This work is greater than me, it promotes the same model of capitalism based on integrity as a primary diver of success.

I want to help other people feel like I did when I was given the chance to drive the Ferrari off that lot, the feeling of pride, self-worth, and assurance to know I can in fact achieve.

Can you tell us about a ‘bleeding edge’ technological breakthrough that you involved in? How do you think that will help people or change the world?

Yes! One brand I’m currently consulting with is a transit company looking to change the way people use public transportation. Subway, bus and metro rail riders across the country, both within big cities and in the surrounding areas, will attest to the frustrating inefficiency of the transit system. Lower income commuters who live in rural areas or outside major cities are especially vulnerable.

Here’s how the technology works — currently most transit brands utilize simple magnetic cards that commuters refill and swipe to board. The problem is, all of the data about how they travel, when, where and how often — is trapped inside every individual magnetic strip.

The brand I’m working with has created a cloud-based technology that leverages data from riders to learn patterns and to let people know when trains or buses are arriving. This means that instead of waiting on a platform, you could be sitting at a coffee shop and alerted when the train is coming — all through a tiny chip. The data this technology provides allow transit providers to make bus routes more efficient, will let people know how far apart buses are, and limit how many unnecessary vehicles are on the road

Frankly, not everyone can afford Uber. Through this technology, not only is the user experience for a commuter improved, but we are empowering people from all socioeconomic situations the ability to move freely — regardless of income.

What do you need to lead this technology to widespread adoption?

In promoting widespread adoption for any technology, it must be simple, easy to use and provide real value for the end-user. If a company can get that golden recipe down, widespread adoption will fuel itself.

Is there a person who you are grateful towards who helped get you to where you are?

My wife and my mother. My mother was incredibly self-disciplined, more so than anyone I’ve met. She was committed to advocating for the socially underserved and the ignored pockets of our fabric. She taught me the importance of integrity, giving back and respect for all life.

In a similar vein, my wife has shown me the value of transparency and remaining honest. She is the most open person I know and always stays true to her values. This inherent sense of honesty has been a linchpin of what I’ve carried through in business. She is my best friend, partner, and mentor. When things get difficult she holds me high for over 15 years.

How have you used your success to bring good to the world?

After I made my first $10M, I took a step back and realized my biggest satisfaction in my work was the overarching theme of helping entrepreneurs succeed, spreading the wealth and giving back.

Unfortunately, standing in the way of this is a concentrated reservoir of money that resides in the bank accounts and portfolios of the 1%. These are the folks that share the stagnant, boys-club view of underpaying women or brushing off the importance of diversity and enrollment in politics for the benefit of companies. This leadership is why so many corporate brands remaining fixed around intolerant ideas.

On the other side of the coin, scrappy, young entrepreneurs typically believe in the value of social contribution, knowledge, and charity to propel forward societal evolution. They understand the importance of ongoing improvement. Only through strategic growth strategies and eventual exits are these entrepreneurs able to gain wealth.

I can do better in the world by not just injecting personal capital towards the success of these companies, but by sharing my knowledge and tools with entrepreneurs to help them be as motivated to give back as I have.

What are your “5 Things I Wish Someone Told Me Before I Started”?

Seek out mentors that fill your gaps

· I learned early on that in order to grow both personally and professionally I needed mentors to guide me along the way. As I grew, I began to seek out people who could teach me and fill gaps in the experience and knowledge I didn’t have. For example, the CEO of the brand that purchased my biotech company taught me nitty-gritty business procedures around supply chain logistics, marketing and how to scale. Another mentor taught me the importance of finance, business models, and governance. Seeking out people that are smarter than you in the areas you are lacking is critical.

Always take the high road

· After I moved to Colorado and began working in banking, I created a broker business with a man who taught me the importance of “taking the high road” — and how integrity achieves the best thing for all parties. Even if it means making a business decision that may not be popular at the time, in the long-term, this has benefited me more times than I can count. I have a following of people who know by personal experience what I stand for and will not compromise.

Stay humble

· Before all else, having a strong sense of humility and gratitude for what you have is your most important asset. Staying humble gives you the space to remain open to learn and grow as a professional. The more you think you know the less you will. Personal growth is achieved through engagement — and it’s important you don’t let that become stagnant. Money is a reward system but its only another tool. How you use it is what determines your legacy. Stay motivated by the change you want to make in the world and the profits will follow.

Surround yourself with honest people who carry similar values as you

· Recognize your value and empower yourself by bringing people into your life that will help you grow, not the opposite. Make a commitment to build relationships with people that see your value and remind you of it every day. Your values are the compass that motivates and drive two-way engagement with those around you. Your disposition and characteristics will be picked up by those around you, inspiring them to get the work you need to be done.

If you could inspire a movement to bring good to people, what would that be?

· During my first company exit, I gave $3M to people that had worked for me — way more than I had any obligation to do. I saw them pay off student loans, purchase homes, get married and put money away for their kid’s college. I saw I was able to make a life-changing difference for them. After that exit, I recognized that other people like myself also do this and value giving back. My goal in writing ‘Meet the BOSS’ is to inspire a movement for entrepreneurs to eventually replicate the gift I had provided for those employees, that they earned.

What is your favorite life lesson quote? Why?

“There is nothing noble in being superior to your fellow man; true nobility is being superior to your former self.” — Ernest Hemingway

So many people in business miss the importance of this concept. Both professionally and personally, I live every day with the notion that how much you give back defines your true wealth, not how much you keep. ‘Meet the BOSS’ is about Kaizen agile change, evolution, and the idea of continually working to improve where you are now in comparison to where you used to be.

You cannot build a company alone, whether you want to admit it or not. Those you surround yourself with, those you train, those you mentor and those you develop — do all those things for you as well. Building a business is a team sport, and you win or lose together. I’ve seen time and again that with the right guidance these companies founders can win. The key is staying humble and taking to heart the fact you need your team, just as much as they need you.

I feel the opportunities I’ve had throughout my career have provided me with the knowledge to help entrepreneurs grow and define an exit strategy from Day One. Spreading the wealth of his knowledge has been my guiding north star when writing this book.

Here is how to get in touch and follow me on social:

https://www.gregoryshepard.com/copy-of-about
https://www.linkedin.com/in/gregshepard/
https://twitter.com/gregshepard_?lang=en

Instagram: @GregShepard

https://www.facebook.com/GregoryJShepard/

For all press inquiries — contact Olivia Ludington ([email protected])

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