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Episode 62: S6E7 – Move On, Fail Forward

  • By dbllawyersv2
  • November 22, 2022
  • Season 6

On today’s episode, Tom Dunlap chats with Larry Sharpe about his time in the military, how he became an entrepreneur, and some of his life lessons.  

Looking for guidance as a young man, Larry joined the military and learned invaluable skills he has carried over to other fields. He tells the story of how he launched his entrepreneurial career, as well as the lessons he learned the hard way through his company. Now the managing director at Neo Sage Group, Larry coaches, trains and consults leaders in how to better impact their team. 

Listen to Tom and Larry discuss entrepreneurial lessons:

How the Military Impacted Larry (1:59) 

Larry discusses how the military gave him the necessary guidance and discipline as a young man after the death of his father. He carried the lessons he learned from the military to every aspect of his career, especially his ability to always keep moving forward.  

Larry’s Path to Entrepreneurship (5:46) 

Larry pursued entrepreneurship as a way to aid his mother, who was struggling to find a job after her felonies. In starting a trucking business, he hired his mom and began cold calling clients. It wasn’t until he left the business to work elsewhere that he realized he had caught the entrepreneurial bug.  

Fail Forward (10:20) 

Larry touches on how setting a goal and defining the outcome you want is key. If you’re running away from something, you’ll inevitably mess up. If you’re running towards something, you’ll find a way to succeed. Eventually, you might fail, so you may as well fail forward.  

Larry’s MBA (12:00) 

When Larry started his second business, a distribution company, he earned his real-world MBA. Unlike his first business where his mother handled admin work, Larry now had to make the leap from just selling to running a functional operation. He learned quickly just how much he needed to learn. 

The Employee Mindset (14:13) 

In Larry’s first year at his new business, he was still in the employee mindset. To him, he would show up, work hard, and assume he’d get paid. What he failed to realize is that when it comes to being an entrepreneur, that’s not enough. He needed to close deals and generate revenue, whether it took 1 hour or 24.  

By the time he sold the business, he had learned a lot, the hard way. He believes that what he built in 2 years, he could’ve built in 3 months. Yet those 2 years taught him how to effectively run a business, which he would carry with him into his next venture.   

The Entrepreneur Mindset (18:45) 

One of the best lessons Larry takes away from his second business is that everyone needs an entrepreneur mindset, whether or not they run a company. Be invested in your job, take ownership of it, and most importantly, communicate accurately and effectively. 

Being good at what you do is simply not enough anymore—you must get results.  

Neo Sage Group (22:29) 

Larry breaks down how he would pitch himself to companies that were struggling, provide a low-risk option, and turn the company around in a few months. This eventually developed into the Neo Sage Group, a consulting firm that provides training, coaching and much more.      

Running for Office (26:39) 

In 2018, Larry ran for office because he was unhappy with how New York state was treating business owners. While he didn’t win, his running exemplifies another belief of his: be a big fish in a small pond. In other words, micro-target, find your niche and you will find success.  

Three Pieces of Advice (31:16) 

In wrapping up the show, Larry gives his three pieces of advice. The first is to always keep moving forward. Whether you’re an entrepreneur or not, Larry also encourages you to own your job and ask yourself what results you truly want. Lastly, he reiterates being a big fish in a small pond. You’ll move up to a bigger pond, and eventually, the ocean.  


TomDunlap – LinkedIn 

Blackletter – Website 

Dunlap Bennett & Ludwig – Website 

NEO Sage – Website

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