Enterprise Building Challenge Stories

from Pat Alacqua

Harness Power of Insight from Experts Who’ve Been There

 

A Message To Start Your Journey: Explore Entrepreneurship

Alester Spears found his signpost at 53. It’s never too late to start on the right career quest.

 

If Alester Spears had it all to do over again, he would be his life’s engineer right out of college in 1991.

He was part of that generation that mostly followed a corporate paint-by-numbers career path. His father, who was his hero, did the corporate thing and Major General Stanhope Spears had a remarkable run in big business before setting sights on a 16-year political career at 58.

Alester found corporate culture was different in the 90s when he set out than in his father’s era. Alester felt less loyalty from the C-level. There was more bottom-line existence. Profit and growth are worthy goals, but why should profit and growth be so one-sided. Email and cell phones meant you constantly had to be available…didn’t matter the day or the time.

It took Spears almost 20 years, but the light finally came on, like it does for so many pent-up entrepreneurs, and he grabbed the rudder to his career. Like his father, Spears did a successful course correction.

“I just wish somebody would have said to me, ‘think about what you really enjoy doing and then back into your skill set’,” Spears said. “If you do that, you're not doing something that you really don't love.”

The flashbulb moment for Spears was when his IT healthcare company hired an outside consultant. This person did not know the industry, or the company Spears was working for. When word got out about the consultant’s contract and how much they were being paid, Alester said it was a “no-brainer” to put out his own shingle as “consultant. 

“I knew the industry and I wanted to control my schedule, and control my income,” he said.

Alester decided to set up his career in service to himself first, not a company. Because of his decade of healthcare IT experience, he jumped into being an IT consultant in health care. He traversed this space for another decade. The job he really coveted was in real estate and a chance to use those people skills he acquired from a pair of master extroverts, his parents.

Spears is 53. It’s never too late to jump-start a sometimes-stalled career, or find your true north, he said.

Use What You Enjoy To

Back Into Your Skill Set

 

And off he went.

While Alester was forging a new career path—and succeeding in a big way—he kept his sense of gratitude, especially with his parents, who were his business role models. 

In 2018, his father started to slip with Alzheimers. Alester’s sense of gratitude and duty was at least as strong as his sense of entrepreneurship and he became a part-time caregiver. Then COVID hit and soon his mother started her own decline.

Spears was transitioning from health care IT to real estate when his mother needed him most. He would not have the same regrets and second thoughts as he had with his career path. While he kept his real estate venture warm, he dove into the care of his mother and still says today he would do “nothing” different in designing her care plan.

The lesson for entrepreneurs out there is you do not have to sacrifice family for career. Spears was able to rev up his real estate dealings when the time was right.

“She gave me a poem that basically said the world is your oyster,” Spears said. “God gave you every single thing he granted everyone else. It’s up to you. The poem highlighted that we have the capability of doing what we want to do and be successful at it.”

Entrepreneurship is a state of mind, which is also something Spears acquired from his mother, Dorothy, who was known as “Dot.”

Alester said his mother owned her own beauty shop when she was in her 20s. She gave it up to raise a family. When the children were old enough, she re-started the business so she had her own budget. Dot was independent and did not want to be the stay-at-home wife who did ladies at lunch or took tennis lessons, Alester said.

“She didn’t want my father saying to her ‘this is the amount of money you have every month to spend’,” Spears said. “My mother was the kind who would always go against the grain. Her lesson was ‘don’t be pigeonholed. This is your life. Don’t allow other people to distract you’.”

Fortunately, Alester’s father, Stan, was also a risk taker and would push the envelope. While reinventing himself at 58 as The Adjutant General of South Carolina, he bucked the system and refused to be beholden to one political party. His focus was on his troops and the people of South Carolina…the people who voted for him… not a political party. Something to be admired in today’s world.

What else can Alester Spears teach entrepreneurs and business leaders who have percolating ideas and challenges getting there?

 Discovering Mentors 

 

Here is a Q&A about Alester's journey.

Talk about your personal story.

"I attended Hampden-Sydney College, a liberal arts college, and received a Mathematical Economics degree in 1991. Hampden-Sydney provided a great place for me to balance school, a few service jobs, social activities, and leadership responsibilities (service clubs, fraternities, etc)."

Who influenced your career and how?

"Mainly my parents. My grandparents struggled, but my parents put a plan together and worked hard to achieve the things they wanted.  My brother and I were their motivation to build a great life. They put us first with everything and were physically present…family dinners, attended sports events, home from work by 5:30/6:00 without distraction.

"They were both extraverts and helped us build strong social skills. My mother gave me a poem that basically said God gave me everything (two hands, clear mind, etc.) that he gave everyone else to be successful in life…it was up to me. I still have the poem.

"I was also very fortunate to meet great business mentors along the way. Those who would inspire, recruit me for jobs or opportunities and allow me to bounce ideas off them.  The secondary benefit is they became great friends.

"I was also very fortunate to meet great business mentors along the way. Those who would inspire, recruit me for jobs or opportunities and allow me to bounce ideas off them.  The secondary benefit is they became great friends."

Please tell us how you got started on career path.

"My career path has taken many turns. In a nutshell it boils down to “who you know.”  My first job out of college was at a bank. I interviewed with them because a childhood friend worked for them.  I had already been on multiple interviews with multiple companies, but nothing materialized. This foot-in-the-door helped me get a job at a bank in Tennessee. From there, I met a friend who offered me a great job (three times my bank job salary) in the automobile finance industry.

"I was there for a few years, but the hours and stress burned me out. However, we had a friend who did the advertising for the car dealerships who introduced me to an HR friend at a Healthcare IT company.  I got hired at this corporate company in sales and it started my 27-year Healthcare IT career. From there, I moved up the corporate ladder through my network of friends and great mentors.

"Eventually, I realized my strengths were managing sales teams, start-ups and helping reorganize sales organizations. I started up a healthcare IT company but picked the wrong business partners. I loved the entrepreneurial spirit of it and realized it was my relationships that carried us as far as we got.

Leverage Strengths

Move Career Forward

 

"About 13 years ago, I was back at a mid-size company when we got a new President. He hired a consultant who was outside the industry and failing miserably on the internal projects. They demotivated the entire sales team (inside and outside). Word got out how much income the consultant was making. I realized then that being my own boss was what I needed to do. So, I started my own consulting company and did it for over a decade. Sometimes you have to turn lemons into lemonade.

"Once again, it was relationships and friends that helped me become successful. I enjoyed the projects but soon got bored with the industry. I was basically hired to do the same thing over and over again.

"Real estate had always been a fascinating interest for me. So, at 52, I got my real estate license and started my real estate career back in my home state of South Carolina.  My family and network of friends were still strong in South Carolina, plus we had owned a beach house for 45 years on the coast. I am grateful every day that I made the change.

“It was relationships and friends that helped me become successful.”

Why I Didn't Start

My Business Sooner

 

Love Many - Trust Few

Always Paddle

Your Own Canoe

 

Talk about any meaningful moments in time on that journey that led to next steps on path that others might find impactful when considering their own career journey.

"I should have picked an industry I was passionate about early on (real estate), instead of what I thought was the “right” thing to do. Two, I should have started my own business much sooner (before you get use to the corporate money). Three, I should have not given in to the guilt of corporate life. Four, I should have learned to leverage my entire friend network much more early on.

When facing big challenges in general

What keeps you stuck?

"Usually, the money and relying on others. Like my cousin says…and this makes a great toast at parties…Love many, trust few and always paddle your own canoe.

What typically has you frustrated?

"Lack of action. I hate not making decisions because that is really making a decision to do nothing. I’d rather try and fail then not to try at all.

What keeps you up at night?

"My best ideas come at night and my mind races at night. Usually, it is going over and over in my head about my actions and if I made the right decision with those actions.

What do you want more and/or less of?

"More real action, less busy work. I like to put things on autopilot. I don’t like people (or traditions) telling me we can’t do/try something. I don’t like people putting monkeys on my back.

 Keeping Me From

Taking Action

 

I Wish This Was Easier

 

What do you want faster?

"Everything. I hate it when people waste my time. I also don’t like unorganized people… i.e. they do a project late and it holds up everyone else and/or cuts into my time. This happened all the time in corporate America. Someone drops the ball, gets me something I need late and then it cuts into my personal time to get the project done.

Tell us about a specific challenge you have taken on:

Describe the problem or opportunity you faced?

"I switched careers in my 50s. People knew me as a Healthcare IT guy but in reality, no one outside of the industry (friends/family) really knew what I did.  My hobby was real estate, and my partner was a high-end luxury home builder in Atlanta so I worked with him on several projects in tandem with my normal career.  When I switched careers, I had to rebrand myself.

"I hate not making decisions because that is really making a decision to do nothing. I’d rather try and fail then not to try at all. The answer is always no if you don’t ask."

 

Give us a snapshot of how you had to work through and share a few strategies or tactics that worked for you. 

"It is mostly your Sphere of Influence (Friends, Family, Business contacts) to leverage for real estate transactions.  So, I basically had to put together a Business Plan wrapped around B2C sales instead of B2B sales for myself.

"B2C sales is a different animal than B2B sales. It requires you to be much more personal in your approach. I had to leverage my friend network, but I also wanted to leverage my business network, as many people look to the South Carolina coast for retirement or vacation homes.

"Additionally, I knew my strength in real estate with outsiders (those moving to South Carolina) would be my corporate approach to business dealings as well as my knowledge of the South Carolina coast. So, putting together different strategies for different lines of business was required. Each of these lines of business require different approaches/tactics regarding social media, advertising, social events, etc.

When all was said and done, did you reach desired outcomes? Why/why not?

"Yes, I am in the process and feel proud of how I have set up my business. I am building connections and people are reaching out. So, I know my plans are working.

Your toughest obstacle(s) you faced with above problem/opportunity and how did you overcome it?

"My mother had a stroke soon after I started my real estate career. So, it delayed my full launch plans.

"I was upset emotionally because it was my mother and a little disappointed that I had to slow down my real estate activities because I was really enjoying my new career.  However, to me nothing else was more important than my mother. Family is ALWAYS first. I moved back to South Carolina because my father had Alzheimer’s and my family needed me.

"Now, my mother needed me. Nothing else mattered. While I had to put my real estate on hold, taking care of both my parents was THE MOST important job that I would ever do.  Quite frankly, I could not avoid the inevitable. They were in their 80s; however, both my parents felt loved and appreciated the last days of their lives because I was there, present, holding their hands and telling them.

"When I considered what others were thinking and feeling during this part of my journey, I know this is where I have changed in life.  I no longer care what others are thinking about me (that is a hard task for a South Carolinian). However, I do make a point never to make anyone feel bad when it comes to any of my actions. Honestly, I hope I encouraged people to do more for their parents. We don’t treat our seniors like we should in this country.

 
 

How did you sketch out the blueprint/strategy you embraced to reach your desired outcome/s?

"I project managed my mother’s care using my healthcare background.  I project managed my new business model like I would for a customer in my consulting days.

Where did you turn for answers, i.e., what type of discovery process did you conduct?

"I bounced ideas off my partner. I talked through my obstacles at night (I also get up in the middle of the night and think of ideas). Time management is key. I make a lot of lists.

If you could start over tackling the challenge, what would you do differently?

"Nothing for my mother. I was really proud of how I managed her healthcare/life during her last 10 months. For real estate, I think I would go with my gut on activities and actions. I have the skills, knowledge, etc., but I was waiting to get all my systems in place prior to pushing to do transactions. In other words, sell the product when you have something to sell, not when it is completed and perfect.

"Always do the right thing for everyone. The result needs to be a win/win otherwise it is not a win."

Key To Implementing

 

Balancing Your Gut

With Thoughtful Diligence

 

Why do you think others struggle getting results when taking on their business challenges?

"They don’t plan, make road maps, compile lists. You really need to do a SWOT (Strengths, Weaknesses, Opportunities, Threats) analysis on everything. At the same time, don’t get caught in the weeds. Leverage your strengths, outsource your weaknesses.

What’s the best advice you’ve ever received about tackling business-related challenges?

"Take each one separately. Break them down into smaller challenges. Focus on baby steps. Map out actions. Celebrate the small wins.

Go into detail about breaking down a challenge:

"When I was in health care, people hired me because they had big challenges in their organization that they had to overcome. So for me to walk in and basically understand what the challenge was—and it could be reorganizing a sales team to be more productive, making sure that the sales teams were structured to hit quota, formulating a formal business plan and strategy—I would break the tasks down.

"This is high-level but…

"I had to understand how the organization operates in today's world and understand how the hierarchy and the org chart is arranged…who does what role. At that point I would do a deep dive into the competitive market and what's going on from an industry perspective. Doing a competitive analysis of the services and  products to understand the “special sauce” for the offering is key.

"I would then understand the sales territories and do a geographic analysis to understand where we are having wins and where we are not winning. How does the territory impact product sales? I would continue to stay focused on considering why we are having wins, and where/why we are not. I go further into what is the corporate philosophy. Do the corporate goals align with individual goals and the sales reps’ quotas? If not, then we need to make sure that they align.

"So it is really breaking down all of these baby steps and going through an in-depth analysis in order to build a business strategy and plan to overcome the challenge.

How To Know

You Reach Win/Win

 

What core message you would offer others before they tackle their next big challenge?

"Always go with your gut. Always do the right thing for everyone. The result needs to be a win/win otherwise it is not a win.

How do you keep up with changes in your industry so you can stay on top of new thinking and ways of doing things that can impact your career and company?

"Read, listen, educate yourself. Align yourself with successful and knowledgeable people in your industry. Use common sense. 

“Map out actions. Celebrate the small wins.”

“Map out actions. Celebrate the small wins.”

My Passion

Why I Do What I Do

Reach Out to Alester  www.CoastalLifeIsTheBestLife.com

He loves to share his passion for the low country of South Carolina.