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16 Key Lessons after 20 years as a Serial Entrepreneur

Over 20 years ago, I started my first business. As a successful serial entrepreneur, I would like to share some key lessons with you, so that you don’t have to make some of the same mistakes.

Being a serial entrepreneur is very similar to the education process. Key mistakes and lessons allow you to move to the next grade to experience greater ranges of mistakes and lessons. There is no scale of the speed to which this happens, but there is definitely a journey involved.

1.Don’t kill your passion!

I sit here today and can honestly convey to you that I have the same passion of selling ideas and solutions today as I had over 20 years ago. Despite the myriad of obstacles, pitfalls and naysayers of my ideas, I always found myself in the zone when I’m discussion the core of my solutions. I like to think I’m more sophisticated and aware on how I discuss it and how I read my audience, but I have not wavered on what it is I’m trying to do.

2.Accept your powers

I’m not being cryptic or cute. You have a gift of seeing opportunities before market leaders do. Whether you see them because your experiences and senses crafted you that way, or you have a sixth sense of seeing around a curve in the road, you must accept that it is unique and more importantly, shunned by majority of non-entrepreneurs. Accept it.

3.You are not the cog in the machinery

As a serial entrepreneur, you find yourself being in control of your destiny in closing and satisfying your deals. You are controlling the art of the pitch for lead generation, and you are controlling the delivery to create the customer satisfaction. To us, this sounds quite normal. To others in large enterprises, you’d be surprised of the bureaucracy to change anything. It really does react to customer and market situations like the Titanic to icebergs. Stay nimble. Let the caretakers that buy your businesses create their bureaucracy. You focus on selling it for the greatest value possible because they don’t know how to create.

4.Know what it is you don’t know

I have made a few really bad decisions over the years and they all happen when I’m making decisions without enough information in front of me. While I enjoy debating financing people on approaches and models today, I was originally too focused on business development and execution of mandates to worry about the day-to-day financial management of one of my companies, and my decision was to bring in a partner who had a deeper financial background to do it. Without understanding exactly what I needed to manage better, I ended up picking the wrong partner who was just better at hiding his weaknesses than I was. In fact, this mistake resulted in a huge amount of cash coming out of my pocket for years from bad decisions. I leaned what it was I had to learn, and it was painful.

5.Risk is in the eye of the beholder

No risk, no reward. It is true. But what you learn early on is that, similar to the point above, others don’t know what it is they don’t know, and it is not at all as risky as what they believe it to be. That is part of the sweet spot of being this type of leader. You see the opportunity in such clear pathway to the close of the transaction that you can capitalize well on their fear of risk.

Don’t let others’ view of risk affect your own, other than how you monetize it.

6.Your model doesn’t have to be in a book yet

One of my businesses was a professional services firm, and a very specific niche around business development. I was always proud of the risk reward model I had created in that business, but as we grew, more MBAs were getting hired, and they struggled with my model of success because, effectively, they couldn’t find my business model in any books on how to run professional services firms. It was painful to convince some of them of how the model worked, but ultimately, you have to believe in what it is you’re doing, and work hard to support the vision beyond what’s in your head. But don’t get me wrong. If people don’t believe in your vision, don’t question your vision; don’t hire them or keep them around.

7.Load up on cash when you don’t need it

It’s a hard one to learn until you’ve been through a recession, but no one wants to invest or lend to you when your business is in trouble, but there is always cash available for you when you actually don’t need it. You must raise it and store it then. Ideas and deals take longer to close, and a cushion always helps, and when things are bad for others, and you have extra cash, always a great time to pick up distressed assets or companies.

8.Be your biggest cheer leader

If you are not your business’ biggest fan, then who is? Yes, you want clients praising the business, but your own ability to turn naysayers into believers and staff into disciples is what will set your business apart.

9.Complacency is death

Most businesses might start with an aggressive program and active competitor analysis, but after some success, start to become complacent with their model and the wants and needs of their customers. In many cases, as bad patches hit, those corp costs tend to disappear. Tech is advancing so fast that resting on your offering will cause you to fall quickly when caught from behind. It is that same approach that allows a small business to steal market share from a company that has become complacent at larger size. They think their size mattered in resiliency.

10.Be constantly building a drama for your company to star in

In the absence of all your staff having acting roles in the drama of your company, they will create their own min-dramas that are likely not consistent with your vision. Here is a great example. Picture your current staff climbing a high mountain together. You can picture staff climbing with structure and purpose to reach new plateaus, reconnect lines to pull the next person up. You reach the top of the mountain. You succeeded in your vision/drama to take that mountain. Now picture on the other end of that mountain is long sloping grassy hill that you all walk down. How do you picture everyone walking down? They are in little mini-groups scattered walking at different speeds and talking about different things and people. You didn’t create the next challenge/drama, and in the absence, they filled the void with their own mini-dramas.

Engage everyone and ensure that your polices and incentives are consistent with everyone’s roles in achieving your success, and after you celebrate achieving it, update the objective and roles in your net drama.

11.Money isn’t there until it is

The thrill of investors indicating interest to invest or lend is extremely gratifying and satisfying. Hearing people indicate that they want to fund your vision is mind-blowing. It is pure validation of your vision and work.

But, “the devil is in the details” must have been phrased by serial entrepreneurs. These types of private investments aren’t rather investee-centric. There are many nuances and risks involved, from the investor perspective, that you cannot and must not put all of your eggs in one basket. Until the deal is signed and the check is cut and cleared, do not become enamoured with the notion and be blind to others.

12.Friends and family are critical

I don’t know of many serial entrepreneurs who haven’t hit bad patches. The problem with being a serial entrepreneur is that your total intrinsic value of knowledge, experience, contacts, deals keeps growing, but there are periods of lack of liquidity or ability to monetize. You know exactly what I mean.

In my experience, family and friends have stepped up when called upon to throw life lines and support, and it shouldn’t be seen as a crutch but a sign of the type community you need to surround yourself with. If your own friends and family don’t believe in you, you will have far bigger issues making things work. It would be like the comedian who gets no laughs with family and friends.

13.Know your strengths

While I always felt I was aware of my weaknesses and did my best to mitigate them, there is also a need to accentuate your strengths. If you know you’re a great salesperson, don’t spend most of your time in operations.

As well, I know that my strengths are more valuable in startups to growth mode. I know I want to build things that become mature for others to run. I learned to think in terms of de-risking opportunities and selling them to lower-expectation money.

14.Invest in people, ideas and innovation

From an early age, even before I started my first business, I believed in investing in the principal of every relationship and only borrowing from the interest. That investment spans decades and has enabled me to build and nurture a large network of contacts across the globe. It’s not that you are leveraging every contact all the time, but I think of it as investing in my pipeline of assets to deliver my energy streams around the world, and at some point they may be used more than others, but I have never ever taken them for granted. (Right now I’m wondering why I haven’t done that with RRSPs…)

15.Create Content

In the days of social media this is more common. We learn so much over the years, and it is crucial for your company vision/drama, customers and investments in people, ideas and innovation to share your thoughts and lessons with your audiences and really think through how they may help others, and present them in the different media outlets.

If someone were to compile the total sum of your public posts of pics, videos, blogs, company info, volunteer info, posts, you should be proud and it should be consistent with the values of who you are and what you have built in your businesses.

Share information that you would be proud of and underpin your vision.

16.There is no such thing as failure, only varying degrees of success

Don’t get stuck using large enterprise equivalency of success. Their metrics are on large mature businesses.

Focus on bite size chunks on what delivers success for you and your businesses, and what you’ll find is that sometimes what others view as failure is really just the lesson you needed to learn from to refine your next offering. Keep learning from every interaction, and find ways of mining the value in either real-time or after the fact. That is part of your value as a person.

I have so many more thoughts and lessons for you, but I think these should motivate you to keep driving the leadership in your family and communities.

I dedicate this post to my friends and family who have been so supportive of me and my ventures for over 20 years. There have been ups and downs, but they have always been helpful, thoughtful and resourceful when I needed it.

I would appreciate your comments and feedback.

One reply on “16 Key Lessons after 20 years as a Serial Entrepreneur”

Dear Mr.Carnevale,

So glad that I connected with you and have been following all your posts. This particular, came at the most opportune moment for me personally. I have just established a solar services firm in my home country and all these 16 points, to me will be used as a guide that the firm is going in the right direction.
With this, I would also like to share a reading ‘Reinventing organization’ by Frederic Laloux. It is all about transitioning towards a higher state of human consciousness to develop an organization with a higher calling. Please do give it a read. I am sure you will relate to it.
Keep sharing, budding renewable energy enthusiasts need mentors like you.

Regards,
Hatim Mustafa

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