VENTEUR chatted with Sandra Guibord, CEO and Founder of Sandra’s Wine Life, about her entrepreneurial journey. Guibord has over two decades of experience in entertainment and business. A former Wilhelmina model and actress in soap operas, network television series, films, and corporate spokesperson roles, Guibord is now a preeminent guide within the wine and spirits community. 

Guibord assists financial institutions, law firms, tech corporations, and nonprofits with entertaining their top clientele and senior executives. She has made the often-vexing world of wine enjoyable through her fun, festive, and informative approach that wine enthusiasts, from novices to connoisseurs, have received well. 

CEO and Founder of Sandra’s Wine Life Sandra Guibord / Photo by John Fortunato

The Journey

The entrepreneurial journey is one of self-discovery. What have you learned about yourself while building your business?

The entrepreneurial journey is definitely one of self-discovery, and as long as you keep building and working, you keep discovering new things about yourself. 

It never stops. 

In my past careers, I had always been in a position where I had to answer to partners and was not able to execute immediately on my ideas. 

While building my business, I also built better confidence in myself. I learned right away that I could be the one to ‘lead the pack,’ take charge and spearhead movements. 

I did not need the approval of anyone anymore, and I found that I could take on even more than I ever thought possible. 

This one self-discovery has been so crucial in my journey because it gives me a solid foundation to keep building my company. No company will succeed if the person does not believe they can reach their end goal and keep leading themself to greatness. 

The entrepreneurial journey is often lonely. Have you experienced loneliness as an entrepreneur?

There is a time when you are a new mother; you are awake and caring for your newborn baby in the dead of the night or the early morning hours. You feel as though you are the only person awake in the world, and there is no one else around experiencing what you’re experiencing. 

It is similar to building your own business. 

You feel like you're doing something no one else is. It can, at times, be isolating and lonely. However, talking with other entrepreneurs, finding common ground, and sharing ideas have been incredibly uplifting in the long battle, and how I overcome those feelings when I experience them. 

There is no better help to overcome loneliness than surrounding yourself with people who love you, understand you, and can provide a shoulder to lean on.

The Psychological Warfare 

Entrepreneurs generally sleep less, work more, and let their health slip. This combination, combined with loneliness, often results in insecurity, self-esteem issues, and low self-worth. Have you experienced any of these issues as an entrepreneur?

Of course, there have been some dark times starting my company. There are dark times no matter what path you choose to take and what business you decide to open.

 It is incredible how powerful and paralyzing self-doubt can be, and there is no question that I have had to experience that throughout my journey. 

There were times when I woke up and went to bed with the running thoughts that I would be a failure, that I won’t be as good as the rest, and the list goes on. 

There are still times like that.

In my long journey as a mother and an entrepreneur, I have learned to overcome those debilitating feelings. I have to dig deep and find that glimmer in all of us. 

I started asking myself, “Why not me?,” “Why shouldn’t I be the one to succeed?” instead of listening to that doubting voice in my head and letting those feelings of insecurity and low self-worth get farther from me. 

It is still a battle, but once you separate those feelings from the bigger picture and your goals, it gets easier, and you can overcome it.

Newer entrepreneurs often equate their personal success with the success and value of their business. If their business fails, they are a failure. If their business succeeds, they are a success. Have you experienced this warped perception of reality?

It is nearly impossible to build a business by yourself from the ground up and not experience failure, roadblocks, and negative feelings. 

When I started building my business, I kept this huge theme in mind throughout the years to experience that warped perception of reality as little as possible. 

I have loved the mantra “fail big,” and that has been something that’s guided me through the ups and downs and the lows and highs that come with being an entrepreneur. 

Making mistakes and having some failures is how you learn to build your business and yourself better, essentially. Therefore, to keep my head on straight and not get misled by warped perceptions, I welcome failure and see it as something that keeps pushing me onward.

What are your three biggest fears as an entrepreneur, and how do you manage those fears?

My three biggest fears as an entrepreneur are the financial stability of my company, the inability to scale, and not being organized enough. 

1. Financial Stability

I, of course, as all entrepreneurs are, am concerned about the financial growth of my company. It’s something that is a constant motivating factor for me. With two children and a passion for what I do, the concern for this makes me work harder, adapt quicker, and learn more. I’m always in search of new ideas, more innovative ways to conduct business, and incredible talent to help us continue to succeed.

2. Inability to Scale Larger

My biggest fear is hitting a wall in the company and being unable to scale larger to reach my goals. In all honesty, to manage this fear, I just have to keep moving forward and not let it get the best of me. 

I must face it and live with it. There is not much more that I’ve found to manage that fear. 

When you have such high-risk factors, you must be tough and firmly believe in yourself, your service, and your product. You simply can't make it if you don’t have that passion and mindset.

3. Not Being Organized

Another fear of mine as an entrepreneur is not being organized enough, missing phone calls, overlooking emails, forgetting a Zoom call, and the list can go on. As a company leader, you’re balancing so many different plates that some things can fall through the cracks. Thankfully, so many programs and alarms on my computer and phone can help me manage this fear and make it something I can deal with. 

To manage all my fears and concerns as an entrepreneur, I found that having some tough love for myself goes a long way.

CEO and Founder of Sandra’s Wine Life Sandra Guibord / Photo by John Fortunato

The Mistakes

What are three mistakes you made early on as an entrepreneur, what did you learn from them, and how can others avoid these mistakes? 

1. Having Too Grand an Approach and Needing To Scale Back My Services

While I don’t necessarily think it’s a mistake to have a grand vision, I believe it needs to be feasible within the timeline you set for yourself. 

For example, I’m currently on the first leg of my Northeastern book tour to promote my first book, “Find Your Wine Identity.” When planning this tour, I made sure to give myself enough time between each book signing to focus on Sandra’s Wine Life and other aspects of my business, not letting those fall to the wayside because I’m overwhelmed with traveling. 

While my ultimate goal is to continue this book tour across the county, I’m making sure not to overwhelm myself and, in turn, potentially neglect other important aspects of my business.

2. Waiting Too Long To Launch My Company

Honestly, I never fully felt ready to leap and officially start my company. To launch Sandra’s Wine Life took the encouragement of very valued people in my life. 

When they offered their own time and relationships to help launch me, I knew when I had the support of these very respected friends and colleagues and knew it was time to do it. 

I learned that confidence is key, and once you take the first few steps, it gets easier and moves forward more smoothly than you had scared yourself out of thinking it would be.

3. Not Having My Social Media Strategy Early On

Nowadays, everyone is tuned into the world via their devices (e.g., cell phones, computers, iPads, etc.). We have access to endless information at the end of our fingertips, and social media is one of the ways we receive that information and create meaningful connections. 

As a business, social media attracts customers and is a way to receive their feedback and build loyalty. 

Early in my career, I wish I had taken the time to hire a specialist and build that to be a bit stronger. 

Luckily, it’s never too late to start, and I’m learning daily the importance of social media calendars, plans, and interactions.

What are three things you see that are often overlooked by entrepreneurs you encounter, and how can other entrepreneurs be aware of these things from the beginning?

1. Utilizing Your Network

Do not be afraid to reach out and start asking for help, guidance, and introductions. I’ve received a lot of business from previous connections, connections, etc. I think other entrepreneurs should realize that it isn’t a burden on someone to reach out and ask them for their help. I think many people get stuck because they don’t want to be a bother or nuisance. I always think that if one of my connections asked me for help, I would be more than delighted and excited to lend a helping hand.

2. Be Prepared To Work Seven Days a Week, but Don’t Forget To Take a Break

The latter is very important and something every entrepreneur needs to remember throughout their journey, which I think most overlook. 

I realized this early on when I was extending myself too far and burning myself out. 

When I did this to myself, it was worse for my company and my mental and physical health than simply not working. 

Not taking a break and rejuvenating decreases productivity, increases negative feelings, and overall makes things more challenging. 

Every entrepreneur, and the average person in general, should be aware of their week and map out a couple of hours a day to take a well-deserved break.

3. Break Down Your Huge Goals Into Small Achievable Tasks

I have learned that doing this allows me to accomplish more in a more realistic time frame and relieves unneeded and unwanted stress. Managing your time and company becomes easier when you break down the bigger picture, monthly or yearly goals into smaller, daily, or weekly tasks.

The Successes

What are three seemingly insurmountable obstacles you’ve faced as an entrepreneur, and how have you overcome them?

Any entrepreneur faces enormous obstacles throughout the lifespan of their company. It never stops, so I don’t ever let myself think that I have passed through the storm. However, to be honest, I never felt that I had insurmountable obstacles to face. Again, of course, I had great leaps and bounds to face, but the most important idea I kept in mind was nothing was ‘insurmountable,’ nothing was going to be impossible for me to overcome. Because of this mindset, I could avoid detrimental feelings about my work and company and keep pushing through. 

What are three ways you have managed to boost your productivity without causing burnout?

1. Make Family Time a Priority

When spending time with my family, I have high spirits and feel so proud of what they’ve all accomplished, and it becomes clear that although I’m building my company for myself, I am also doing it for them. 

I always want to work harder for them and ensure I’m available. Having that important family time always boosts my confidence and productivity and allows me to keep going without negative feelings or burnout.

2. Exercise Is Essential To Clear Your Head

Every morning I make it a point to get to the gym before I start my day. Beginning the workday after a great workout gives me a clear head and a positive attitude to take into work. 

Starting the day with a workout helps me increase productivity and prevents a short fuse. 

3. Having a Partner That I Can Share My Concerns With and Talk Through Issues

The fact that I can vent at the end of the day, talk through issues I may be having, or share accomplishments with someone who is extremely important to me and understands me helps me remain level-headed and prevents the feeling of carrying the weight of the world on my shoulders. 

The Advice

How can newer entrepreneurs develop a healthy work-life balance even when it seems like an impossible task?

Newer entrepreneurs need to be aware of what causes their burnout, negative feelings, self-doubt, etc. They should  find outlets to relieve their stress, designate time for relaxation and rejuvenation, have a sound support system, and have tough love for themselves.

What three key pieces of advice would have made your entrepreneurial journey easier, and why? 

1. To Be Open to Changing or Shifting My Product and Service

You have to be open to suggestions and solutions that are not on your pre-planned radar. For years I presented in person in front of a crowd. When the pandemic hit, I quickly pivoted to virtual wine tastings.

2. Utilizing Your Network

Again, using your network is an integral part of the process and should be started immediately. No one should feel uncomfortable reaching out to others and asking for help, guidance, or even words of wisdom. People are more willing to help than you think.

3. Not Letting My Fear of Failure Get in the Way

As a woman in this business, I knew I would have to stand out from the competition and prove my worth as an expert and businesswoman. But when you’re building something from the ground up, mistakes can be made along the way, and I had to realize that those mistakes didn’t mean I would fail. 

They were just bumps in the road to help me achieve my success. But I found the best way to stand out was to bring my experience into my current business plan. 

I co-founded a tech event company that sharpened my skills in growing the community and working with top-tier sponsors. 

This experience has been invaluable in the growth of my current company. 

Topic Contributors

Questions based in part on topics and comments provided by:

  1. Alicia Nagel, Founder at Alicia Nagel Creative
  2. Rob Volpe, Chief Executive Officer at Ignite 360
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