Playing To Win: 8 Entrepreneurial Commandments You Should Live & Die By

You know how people say hindsight is 20/20, well it definitely is. I wish I knew some of the things I know now, I am damn sure I would have spared myself some of the mistakes I made over the course of my trep journey. As an entrepreneur, we can all agree that bootstrapping your business is hard as hell, so who wouldn’t want a few top secret tips whispered into their ear from someone who has lived and experienced it? Why play at all if you are not playing to win.

So read on about some of my entrepreneurial pivotal lessons, some say “aha moments”, well I like to call them “Entrepreneurial Commandments” to be dramatic (I tend to have a flare for the dramatics, haha) that has helped me win in my businesses. These are the 8 things I know for sure!


1. Great strategy alone won’t win the battle, flawless execution will

I talk about this a lot. It doesn’t matter if your business idea is unique, the first of its kind or just another T-shirt company. Chances are, no matter how much of a genius you are, someone else probably has the same exact grand idea as you.

Success doesn’t necessarily come from breakthrough innovation but from flawless execution. It always boils down to EXECUTION. A great strategy or idea alone won’t win the battle.  Success comes from the combination of the idea, great strategy and a bomb a$$ execution. If there is one thing you can take away from this is, let it be this:

Success is 1% idea & 99% execution.

Ideas are a dime a dozen, but the execution of them is few and far between. More than just being a dreamer, visionary or having the mere desire to win, you have to be willing to roll up your sleeves, do your research, ask the hard questions, be a doer and get your hands dirty. You have to do the work, you have to deliver, there are no magical formulas or shortcuts. Winning and success comes from basic blocking, tackling and even pivoting. If you lack in experience, plan to put together a great management team to help you execute and bring those grand ideas to life. Be honest and upfront with yourself and your team, know your strengths and weaknesses and be willing to get help in filling in the gaps to round out your execution team. Remember that the devil is always in the details. Successful execution is about taking the lead, owning the process, understanding the big picture and implementation that could be the catalyst to hitting a home run.



2. Work “on” your business, not “in” it

This has been one of my biggest Ah-Ha’s as an entrepreneur. One of my favorite books that I always recommend to other treps is The E-Myth by Michael Gerber, which draws the important and very overlooked distinction between working ON your business versus working IN your business. In the beginning, so many treps during their entrepreneurial infancy get mired in the details of running the business (raises hand…because I was guilty of this too). I mean, when you are first starting out, it is damn near impossible not to be all in the details. I mean…hard. But the problem is that we become so heavily immersed in managing and running all aspects of our company’s day-to-day operations that there is no time for anything else. While this is necessary at first, you have to remember that a business that can only work with your physical presence is not a business at all. This is working IN your business.

Your business needs to be able to run itself without your constant presence.You have to treat your business like it is a franchisable entity.

So you are probably thinking, but hey… I am not creating a franchise. Yes, that’s true but you have to treat your business like it will be franchised even if it will not. Think McDonald’s or Burger King. The fries and burgers and experience you get when you eat there is the same no matter where you are in the world. Why? Well, it’s because they have very well documented processes, instructions and manuals for how everything works. So no matter who works there (college educated or high school dropout), the same process is followed. So even a dummy can do it. Similarly, you have to create well documented processes and manuals for every aspect of how to run and operate your business. Your business has to be able to thrive and be successful beyond you. This is working ON your business, not IN in your business. It’s all about creating processes.

So 2- 3 years ago, after reading The E-Myth Revisited, you best believe we hulled our asses and went straight to work. We created well documented processes, how-to videos & manuals for almost every aspect of the business….Customer Service, Warehouse Management & Fulfillment, Inventory Management, Marketing, Sales, etc. I have found that the more systems and processes we put in place and implemented, members of my team were able to do their jobs better which also meant they needed me less and less day to day. Hiring new employees is so much easier too when they can start and hit the ground running. So now I have more time to focus on the big picture, overall strategy and the growth of my businesses. Not to mention, I am able to do things like go away on vacation like my recent 10-day European trip to France and Spain without worrying about the business completely coming to a halt.

Remember that a successful business is one where the owner has created systems so that the business can run itself without their constant presence. After you have read The E-Myth Revisited, you will truly be able to grow your business in a predictable and productive way. Highly recommended.



3. Listen to your customers

For me, this one has been an integral part of how I keep my customers coming back again and again. As a entrepreneur, you cannot grow in a vacuum. You need to understand what your customers think of your products? What more do they want? How can you improve current product offerings? Ask for their feedback, good or bad and act on it.

Don’t take the feedback personal when they are not favorable, remember it’s not about you. It’s about them and the problem you are trying to solve.

That is how we have been able to continue to move ahead in the maternity industry and create innovative new offerings. When I first launched You! Lingerie, we started with limited sizes, only offered popular cups B through F. Now we have more options for larger cups up to J and even more supportive features – wider straps, fuller cups  overall better construction. We listen when our customers ask for something new, for variations on our offerings and other ways of achieving goals.



4. Value your time, there’s only 24 hours in a day. Get shit done

Honestly, I feel like entrepreneurs are the busiest people on the planet, seriously! At least, that’s how I feel, LOL. And when you add employees, two small kids (6yr old and 3yr old), a hubby, our home to manage, parents, inlaws, siblings and friends to stay connected with, it seems impossible sometimes to get it all done. And with only only 24 hours in the day, you will quickly realize there’s just never enough time to get everything done.

As an entrepreneur, time is your most valuable asset, hands down.

As a mom and small business owner, “finding time to get it all done” is a common challenge. Yes, it is hard but there are ways to find a harmonious balance between family, business and all the other things that matter to you in life. I could talk in length about it, but to sum it up in the simplest of terms is you have to PRIORITIZE. If you are familiar with Pareto’s Principle (the 80/20 rule), you have to apply this to every aspect of your life. I believe it is absolutely fundamental to every business person, to every human being. If you are not familiar with this concept, it essentially means that roughly 80% of the the value of  come from 20% of your inputs. For example, if you look closely at your business, you will quickly realize that only a small percent of customers account for majority of your revenue. Similarly, in your personal life, if you look closely, you will find numerous examples of 80/20 ratios that will allow you to stop wasting time on those 80 percent activities that produce little satisfaction for you.  (Ain’t nobody got time for that).  Focus on the things that creates the most impact to your business, your family, your life. You will be more productive and most importantly, you’ll be happier. Who doesn’t want that right?

Keep a to-do list and focus on creating time for everything. Believe me when I say, everything goes on my calendar. I mean everything. It keeps me honest and mindful of my time.

Dedicate and allot the time you use for your social media, schedule it in your calender — either an hour or two in the morning or evening.  Social networks such as Facebook, Twitter and Instagram, these things can become time sucks (I am guilty of this too) if you don’t plan or manage them well. It’s so easy to get lost in cyberspace and spend hours on your phone or computer. Be aware of your time and your schedule.

Focus on completing your to-do list. Have a written to-do list where you can check off each item as it is completed. The tangible act of crossing off a completed task is a sign of accomplishment. Get shit done!



5. Brush your shoulders off and don’t be scared to pivot.

Of course, everyone pursuing entrepreneurship starts out thinking their idea is the best in the world, but the reality is that startups are often more complicated than they initially seem. Touché, right? It’s always best to do your research. Do your homework (product, market fit, consumer interest, pricing strategies, positioning, competition, marketing strategies etc) before embarking on launching your new business or product.  So you’ve done all of those things but things are still not looking up. Yes, this happens. That’s what makes entrepreneurship quite the thrill. As treps, we often beat ourselves up when things do not go the way we had planned especially when you are so focused on a BIG end goal. Everything will not always go as planned…no matter how air tight your plans are (welcome to entrepreneurship!). 

Sometimes, even after your research and a very positive market viability report, your business just is not seeing the results or success you had planned for. Don’t beat yourself up over it or give up altogether. Find fruits of success within your failed ideas and use them to move on to a stronger alternative.

When I decided to dive into entrepreneurship with an idea that I passionately believed would rock the maternity industry, I was equipped with my Duke MBA, experience as a brand manager, a serious love (border line addiction) for fashion and a positive market viability that proved that there was white space opportunity for fashionable and affordable maternity and nursing underthings. But without a background in design, I decided that I would partner with a lingerie designer to help bring my ideas to life. And I did. Twice actually. But unfortunately, when both my partnerships fell through a few months into the journey, I decided to take matters into my own hands. I became a student of my work and taught myself everything I needed to know to create and design the best maternity and nursing lingerie products. Yes, it took much longer to launch and I faced road blocks along the way but it was all worth it.

There will be setbacks, get back up and brush your shoulders off

You will win some and lose some. Don’t be afraid to pivot. And you know what, that’s okay too. It is part of the process, so just embrace it and do not let it defeat you.  Allow yourself to make mistakes. Learn from them and move on and like my hubby says, “do not over-rotate on it“.  It will help you appreciate the journey more.  So like Jay-Z said, get up and dust your shoulders off. 


6. It always cost more than your original budget

I am a numbers girl and a planner. So if you are like me, you have done your homework with the numbers to figure out how much money you need to launch your business but it still ended up costing you a bit more.  So now think when you have a remodel project in your home, like say you plan to redo your kitchen or bathroom for $5000 but then it ended up costing almost $6000 or $7000 because you had no idea there was a broken pipe hidden behind the walls somewhere. Same thing here.  Happens every time.

Most entrepreneurs tend to underestimate how long it actually takes to bring a new product to market, while overestimating revenue. You need to be realistic with your projections and you need to maintain a solid balance sheet so that you’re ready for surprises.

No matter how thorough you are, there will be “unforeseen” things, fees etc that you had not planned for in the process of launching your brand. Always give yourself some wiggle room in your budget. Plan for it, the same way you have an emergency fund for those “unforeseen” circumstances. Additionally, make sure you have contingency plans in place to mitigate it. And in the unlikely case that you don’t need it, then you’ll be “cash” golden. Cha ching! 🙂



7. A closed mouth does not get fed

While you may not always get what you want, you must have the courage to boldly ask for exactly what you want.  You have to think about what your ideal outcome would be and then confidently ask for it in a way that shows that you know your worth. When I was first approached by Walmart to partner with them, being the giant retailer that they are, anyone would be willing to do whatever they requested (and at first I was). But I knew that despite my excitement, I had to have the courage to clearly ask for and articulate my own terms/needs that would allow for the partnership to be a win-win. I did and was able to negotiate a term that was favorable for my business. 

File this one under life lessons as well. Especially as a mom and entrepreneur, we tend to put the needs of everyone else above ours – the kids, husbands, pets etc where we try to be all things to everyone. The end result is we fall short on all fronts and end up getting resentful or burnt out. That’s no fun. Who the hell wants that? So the more I am needed, the more I am learning to ask the help of others as much as I can.

The reality is, I’m smart enough to know that I am not superwoman and moving my own needs higher on my priority list and asking for help is therefore not selfish, it’s smart. It’s badass. Life and business is just sweeter this way. 

Oprah is right when she said, you only get in life what you have the courage to ask for. You will never get anywhere if you don’t have the courage to speak up and ask for what you need and why you desire it. Be persistent. Asking for less than you really want whether from yourself, others or life in general does not serve anyone. Be bold. Be courageous, you’d be amazed by how many people are just waiting to tell you YES!



8. Remember to celebrate even the smallest wins

Drinks and sushi after work because we got a new international wholesale account. Hell yes! An unexpected product editorial feature in a major magazine? Let’s order pizza for the entire team to celebrate. We made our numbers this month, let’s do a half day Friday. I look for any reason to celebrate whenever I can. I mean, honestly, life as an entrepreneur is tough as it is, so why the hell not.  We all want to build successful businesses and get to the finish line. But remember it is not a race but a marathon, so you must try to enjoy the ride and celebrate the milestones along the way. If you are always waiting to celebrate only the big wins & successes, you may get burnt out quickly. Plus it allows your team to realize that you appreciate their efforts.


What do you think about my list? What are some of yours? Let’s chat in the comments below. Sharing is caring, right?

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