3 Lessons Learned from Becoming a Serial Entrepreneur
Kate Holden, an Entrepreneurs’ Organization (EO) member, is the president of EO’s Winnipeg chapter and a serial entrepreneur with companies such as De Luca Wonderful Wines and Flaunt. We asked Kate what she’s discovered from being a serial entrepreneur. This is what she shared:
If you’re an entrepreneur savoring achievement with your initially business enterprise, you have likely considered about launching a second small business.
About 30 percent of business owners are serial business owners–and have a tendency to have on the title as a badge of honor in bios and social media profiles. But does it do a lot more than fluff our egos? Is serial entrepreneurship the greatest kind of entrepreneurship and social evidence denoting results?
Scientific tests on the topic give mixed responses. Some demonstrate that entrepreneurs with more than just one venture are much more most likely to obtain success. Many others inform us that serial entrepreneurship is no unique than 1st-time entrepreneurship.
As I put together to liquidate my 2nd enterprise, which I excitedly released virtually seven yrs ago, I want to share what I learned from the achievement and the failure that it introduced me.
Initially, a little bit of background: I ordered, transformed, and grew my first and major business enterprise, a wine retail and e-commerce organization, practically 14 years ago. Like most business people, my lifestyle was fully commited to it.
But in time, items started to modify. I commenced to transform.
As the organization grew, I joined EO, a world wide local community of smart, passionate business people who I could study from. I felt like I had discovered my position. My men and women.
My standpoint started to change. The way I saw the company globe fully transformed. It’s as if I expended a 10 years staring at my corporation from a 100-foot vantage stage, then in an instantaneous, I could see it from 10,000 ft.
The heavy governmental regulation of the wine business stifled both equally my creativity and innate disruptor tendencies. I designed ideas I needed to examine, but the sector wouldn’t let it.
So, I released my next company–a manner retail brand–as my creative outlet. It was the small business I could do anything at all with. An similarly passionate, manner-savvy friend joined me as co-proprietor. We found a locale, secured product or service, released marketing, and I was all set to come to be a (effective!) two-time entrepreneur.
But things did not perform out as I envisioned. Below are three lessons that the working experience taught me.
Lesson 1: Select the proper organization lover and explain your roles
A single of the most major lessons I realized is to make sure all organization companions are self-conscious, clear, and aligned in phrases of:
- 
- what they want out of the business
- what they are going to place into the business enterprise
- why they want the business enterprise to start with



Clarity among partners is usually important, in particular when you might be running other businesses at the similar time. I failed to set up sufficient clarity on roles, duties, or answers to extra considerable questions such as “What’s your WHY for this organization?” My partnership was a obstacle from the outset, and the enterprise absorbed that challenge everyday.
Lesson 2: If you are unable to measure it, you are not able to deal with it
Types, frameworks, procedures, processes: I knew how critical they are. They remained important pillars of my initial enterprise, still I had none of them in my next business.
Setting a obvious and mapped-out eyesight, scorecards for every single employee, a predictable conference cadence, and powerful KPIs for every single metric are all essential to mature and scale.
They are important to sustain passion for the work, as well: If you can measure progress, you can see how considerably you have come. Without having processes, a small business feels (at best) like a lifestyle company or (at worst) a hobby–and I didn’t need to have any additional hobbies.
Lesson 3: Expanding and outgrowing is all right
My next business enterprise was developed as my innovative outlet. Nonetheless, I identified myself in a entire world of smaller square footage, small purchases and returns, and compact margins. I recognized that I had developed as well a lot to hold sensation “little.” I was altering faster and dreaming even larger than my trend keep could.
My major–and most essential–lesson: It is a lot more than ok to outgrow a business, whether it is really your initially business, 2nd, or tenth.
From social media to magazine articles to hearing significant-title influencers give talks, we hear so a great deal about growth–but no one talks about “outgrowth.” What occurs when you grow so substantially that you no for a longer time experience influenced by what you’re doing? I liked my next organization, but I failed to really like the smaller scale of it.
In the long run, my encounter in serial entrepreneurship was not a productive one (still). But I attained priceless takeaways, some of which apply to my wine enterprise, and other individuals which I am going to utilize to my future company.
Growth is a positive, needed point. If you do it very well enough, in some cases outgrowth will come with it. No issue which business enterprise of yours you happen to be constructing, remember: Better to have grown and outgrown than to have never grown at all.