4 Lessons for Starting Four Companies in Four Years



I started on my entrepreneurial path while working full-time in a law firm. I was making a good salary, had a corner office and enjoyed the work. My Sin City Cupcakes co-founder Dannielle Cole called me one day to catch up, as friends do, and from there the idea of alcohol-infused cupcake company was born.
We started the company with no business plan and a lot of enthusiasm. I am fairly risk-averse by nature, so the idea of quitting my (safe) legal job to pursue the business full-time never crossed my mind. In fact, I stayed at the law firm for the first 18 months of business operations. We also bootstrapped the company, as I have done with every company since then.
Every entrepreneur you meet has had a different path and different journey. The best thing you can do is to start your business your way and on your terms — bootstrapped or funded, with or without a day job. But there are a few things I learned from launching 4 businesses in 4 years that can help you make the best decisions along the way:
Do Not Take the Startup Journey Alone
There is no question that an entrepreneur’s life can be difficult and at times, lonely. But you do not have to take on all the challenges and hardships alone. People always tell me, “It seems like you are everywhere! How do you do it all?” I certainly wear many hats, but I do not do it all. There is no way I could. I have strong partners in each of my businesses, who are focused and dedicated to the company in a different way than I am. Our strengths and weaknesses are complementary and result in our abilities to get the job done.
Perhaps you have the funds to start a business but not the time required to initiate it. Perhaps someone else has a great business idea and you are the person with the knowledge to implement it. Start having those conversations with people around you. It just takes the right people at the right time to come together and bring companies to fruition.
Join a Worthwhile Professional Organization
Time is always limited. As a result, any extracurricular groups you join absolutely have to be worth your time and funds. I am personally a member of Young Entrepreneur Council and the Asian Real Estate Association of America. I find tremendous value through these organizations. I meet like-minded colleagues and am able to bounce business ideas off people who have experienced what I am going through firsthand.
Ask your mentors and colleagues what organizations they are a part of. Read and research the feedback you receive to determine what would be the right fit for you. And remember, it does not always have to be an organization directly related to your industry. One of my mentors maintains a membership in an aviation organization simply because he is an enthusiast, yet it is totally unrelated to his software/technology endeavors. Yet, he has received many clients and referrals through his connections within the aviation group and it’s something he enjoys. Find the right fit for you and those ancillary benefits will come forth.
Utilize Current Resources (Including Those Right Under Your Nose)
Work laterally and utilize current resources available now to assist and bootstrap into your next endeavor. You do not have to reinvent the wheel with each new startup. Dreaming big of landing a whale investor and obtaining funding is great, but look to your circle for help getting started. My parents helped fund my first startup. They gave me a no-interest loan on the condition that if the company failed in the first 18 months I would grant them ownership interest so that they could take the loss on their taxes. Luckily, it never came to that — to this day, that same firm I worked for before starting my first company is our go-to legal counsel.
Also, realize that many of the same needs from your first company will be common, if not the same needs in your next company. For example, the package supplier that makes the bakery boxes for Sin City Cupcakes was the first manufacturer we worked with for swimwear packaging for Liquid & Lace. All of my companies utilize the same web branding professional, Ultrabrand, and social media account services.
Start Within Your Community
As a former Miss Las Vegas and Miss Nevada, I am blessed beyond measure in the way that the community has embraced me as their own. Every industry has shown their support. Nevada itself has always been pro-business and business friendly, and while I didn’t grow up here (I moved to Las Vegas in 2010) the community treats me as one of their own. My mentors are some of the most established business people in the country, and most of them have their businesses based in Nevada with an international reach.
It is comforting to know that advice, guidance and assistance are all just one phone call away. Build and cultivate relationships within your local community with successful people you want to learn from. They do not have to be in your direct field or industry. Everyone has something of value to offer. Learn it all.


The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched BusinessCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.

Image credit: CC by John Benson

About the author: Lisa Song Sutton

Lisa Song Sutton, JD, is a real estate investor and serial entrepreneur, holding ownership interests in several companies in the real estate, retail and food & beverage sectors, including the popular alcohol-infused bakeshop: Sin City Cupcakes. In addition to her professional careers, Ms. Sutton is a contributing writer for various business publications and is actively involved in her community as a former Miss Nevada United States 2014. Learn more about Lisa and her companies here .

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