July 23

3 Lessons Vince Whinnery Learned While Transitioning From Startup Entrepreneur To CEO


Today we’re profiling a “behind the scenes” executive, Vince Whinnery, who has quietly built an excellent track record in multiple positions of the C-suite. Whinnery has managed to combine a track record of timely strategy, management and operations to hit several home runs while transitioning companies from startup to a corporate structure. 

While most executives start their career with a graduate degree and then transition into management, and work their way into the executive level, Vince transitioned from an entrepreneur turned executive and developed a unique combination of wins along the way.

From Entrepreneur to CEO


He began his journey in 2002 while in the Air Force and spent 4 years before achieving any significant success. Shortly after separating from the military in 2007, he progressed to the top of one industry, and then to the top of another highly-competitive industry as a solopreneur. By 2013 his focus shifted towards building “real companies” in his words – with operations, a team, and systems making it desirable in the marketplace and attractive for acquisition.

Now at the age of 38 and after more than 15 startups he has refined the process and has an unusually high success rate of building startups into profitable companies. As CEO he was able to pivot fast in 2015 while building an ecommerce apparel company when most competitors went out of business. As COO of TRP, a career development and resume company, he was able to optimize the operations over the course of 2 years helping generate a profit margin of 4x the industry average, and achieved a client success rate of 75% where other top companies have a 5-10% success rate.

Currently, he is in startup mode building a publicity firm with a unique twist that has already achieved outstanding results, and is on track to be valued at $30M in the first 2.5 year. After achieving multiple milestones and being described as  a top 3 Public Relations firm for 2021, the young company is well on its way to success. This entrepreneur has a unique ability to transition companies from startup success to operational companies – something that is a rarity and one of the reasons he has developed a reputation as someone who can achieve big things fast.

Mr. Whinnery states there have been a handful of lessons he’s learned while making the transition from startup to executive that has helped to shape his success. 

Here are 3 lessons he’s learned along the way, in his own words…


  1. Find a way to keep focus on the strategy early on – above all else

One of the most critical lessons I’ve learned while transitioning from startup to achieving solid operations and stable cash flow was to set aside time daily (at a minimum weekly) to review the strategy, and look over all areas of the company. In my early days, I missed a couple high-level critical moves, which effectively crippled the company. I missed it because I was focused on completing tasks for the current milestone at the time, but if I was able to sit in only the CEO seat I would have easily seen the issue, adjusted, and made the correct move. 

Since then I’ve systematized much of the process (particularly while in the early development stage) so I don’t miss these critical steps. It’s difficult while in the early phase due to being both in charge, and also the one doing much of the work jumping between 3 levels (C-level, mid level management, and task execution). I’ve found if you can see the strategy clearly at this stage then it is typically a non-issue during later development stages.

2. Operations requires a level-head and accurate tracking for process refinement

At the COO level it is critical to have a dashboard and track metrics accurately. Aside from achieving the basic requirements and responsibilities of the position, it is essential in order to optimize and streamline everything under the operations umbrella until you turn the business from a lump of coal into a diamond. 

One way to fast track this is to build out processes and systems prior to scaling up the team. While this is difficult in practice, it is more difficult to go backwards and update the systems and get these in place once you have a team used to doing everything differently. 

3. Start with the exit plan from the beginning

Outside of Silicon Valley, I’ve realized most entrepreneurs don’t typically have an exit strategy in place (at least beyond a vague “sell for a billion dollars”). I didn’t begin thinking about this till after a decade in, and really not seriously until the last 5 years. It is critical early on to build the reputation with potential investors regardless of if you plan to use venture capital or funding rounds. This way at a later date the correct groundwork is already in place to make the big moves and cash in. Plan on succeeding from the beginning.

This means setting and achieving milestones are critical in the startup and growth phase. You need to show reliability in execution towards goals while avoiding burnout and hitting a wall. Also this gives investors a way of learning about you and follow your story. Waiting till you’re ready to sell and then looking around and wondering why no one wants equity in your company puts you in a tough position.

The Next Step of Vince Whinnery’s Career…


The progression of Vince’s career has been steady, and continues to move forward fast. As he has said, “While hard work is absolutely required in order to achieve anything of significance at this level, I’ve been lucky and honored to have the right experiences at the right times which helped accelerate my progress, and I’ve met some amazing people along the way as well.”

Despite the relative success Whinnery has achieved at a young age, he has bigger plans for the future. In his words…


“I’m excited about 3 plans coming to fruition in the near future –
1) The rapid success of the PR firm and the future of how we will be reshaping the industry.
2) For a new company we will be starting in the next year or so. I’m not saying more about it publicly yet, and
3) For a nonprofit that is in development which will make a massive impact in the lives of injured veterans living in central Texas.” 


It will be fun to watch his rise in the coming years as he steps out from behind the scenes and takes a more public role. You can learn more about Vince Whinnery at www.vincewhinnery.com on his website or about Amplified Authority.

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