4 Lessons for Starting Four Companies in Four Years

4 Lessons for Starting Four Companies in Four Years

(Image: iStock.com/julief514)

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 an alcohol-infused cupcake company was born.

We started the company with no business plan and a lot of enthusiasm. I’m 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 four businesses in four years that can help you make the best decisions along the way:

Don’t Take the Startup Journey Alone


There’s no question that an entrepreneur’s life can be difficult and at times–lonely. But, you don’t 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 don’t do it all. There’s 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’re 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’m going through firsthand.

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Lisa Song Sutton, J.D., is a real estate investor and serial entrepreneur, holding ownership interests in several companies in the real estate, retail, tech, and food & beverage sectors, including the popular alcohol-infused bakeshop, Sin City Cupcakes. 

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