I think I knew I was an entrepreneur when I was 12 years old.
My “symptoms” were many different weird activities and ideas. On the pre-eBay days, I used to buy used things magazines (yes, paper magazines) and try to buy things cheap and sell them at market price, allowing me to make some profit. In my late teens and early twenties, I was obsessed with bringing new concepts and opportunities to Latin America (I was born and raised in Argentina, where I lived during the first 35 years of my life) from the US or Europe. My first, and probably only, real corporate job was in my early twenties as Marketing Director at Apple (my dream company and dream job for sure). After only three years on that job, I realized that I was not a “corporate guy” and I was not looking forward to spending my time on the corporate ladder, even if this job or opportunity was my “dream job.” I was always dreaming about my own ideas or ventures, always having a true and honest passion for building things that could fix real problems and create significantly better customer experiences and opportunities.
Like many other entrepreneurs, if you are lucky to have some liquidity event in your career, (translation, selling any of your ventures early enough in life in order to have the energy and desire to do more stuff apart from playing golf and traveling the world), you start doing angel investments and help other entrepreneurs build their own ventures. I followed that route and started doing some angel investments in my early 30’s, continuing to do so in a more structured and disciplined manner when I created Vesuvio Ventures almost ten years ago during my early 40’s.
Nevertheless, having 35+ years of experience in business, starting in my teenage days, has helped me to learn some valuable lessons. Today’s blog is about one key lesson that I learned particularly during the last ten years: being humble and learning from your failures. I was wrong so many times, failing even more times in realizing that being an entrepreneur or investor is a humbling experience.
I guess that sounds cliché and probably cheesy, but it is true. When you start your entrepreneurial career, at least for me, it was all in 24/7 building towards building my company. Laser focus, execution, obsession with details, and all the classic stuff that you can read about in regard to building your own startup. After my first exit, I started to diversify investments and time allocation into more things, and, with this decision, came a natural correlation with success and failure ratios. The reality is that your chances of becoming a “successful” entrepreneur that can scale and sell his business or enjoy wealth through the realization of your startup are not very high. Every single credible statistic supports the fact that only a few entrepreneurs are part of that “elite” team. Being an early-stage investor is not the opposite. The VC industry is full of difficult returns for LP’s and GP’s, with a small and privileged group of VC’s who can have successful and sustainable careers in this industry. As a person who did both (entrepreneur starting from scratch and operating companies until they exit as well as an early-stage investor), I had my own “humbling moments” along with my career. I also understand now, that it seems that I have a clear tendency to select “tortuous career selection skills.”
From my own experience, being an entrepreneur is a humbling experience from many angles. In the early days, you are usually ignored by customers, investors, and probably the rest of the world (your family could be an exception if you are really lucky). You will experience the emotional roller coaster of being a visionary genius one week and a moron the next week, as well as the constant feeling of walking a fine line between surviving until the next funding round or customer contracts or both. But, in the end, you are controlling your own destiny, and if you are persistent, work hard, listen carefully, and have the right amount of luck, you will probably move into the small and elite group of successful entrepreneurs. That’s where the tricky part comes into play because you think you learned some lessons and that you should be able to scale said lessons faster, allowing you to enjoy the ride during the next phase in your career. Unfortunately, it is not as easy as that, at least for me. There is some partial truth in this thesis, and, you may certainly take full advantage of the lessons learned. But, like many things in life, it’s easy to say and difficult to execute.
When I started the “investor phase” in my career, my goals were very clear. I wanted to work with amazing young entrepreneurs and help them to build their companies faster and better by sharing my own experience and hopefully adding value to them. These goals were reflected when I started Vesuvio Ventures.
When you start investing (time and/or money) instead of operating your own venture, there is a natural tendency to think that you are still operating day to day instead of just advising or investing in the venture. In my case, understanding this “small difference” took many years and tough learnings. After spending a long time doing early-stage investment, I still think and operate as an entrepreneur and not as an investor, making sure I am always very honest before joining any new advisory or investment opportunity about my own skills and passion.
I finally realized that I greatly enjoy and can be more useful in doing “company building” or “venture studio” activities where I am able to deploy time and capital supporting full-time founders in building ventures and operating as a sort co-founder until the venture is ready to attract additional capital and management skills. I have been spending most of my time around this model for the last ten years and have enjoyed this method way more as well as having built more equity value along the road.
On a parallel basis, I partner and work with big corporations or private equity companies when they are looking forward to investing or partnering with early-stage tech startups and they need some external help to identify and structure these investments or partnerships. This corporate venture capital (CVC) partnership is strategic for me as a way to link startups with corporations and accelerate opportunities.
One of the few benefits of becoming old (at 52 years old, I guess that I qualify in the “old people category.” Something my son and daughters keep reminding me of all the time) is that time brings you perspective. You are able to remember so many mistakes and failures in your life and career, hopefully learning to skip those mistakes and focus your time and energy on the people and things that really matter. I chose two activities for my personal business life and career where failure is the norm and success is the exception. Very few entrepreneurs are able to succeed in building ventures that allow them to prosper economically and live a balanced life. This may sound harsh or pessimistic, but unfortunately, every single statistic on the entrepreneurial journey supports this reality. Nevertheless, I think that I chose the right career for me and I’m grateful that I was able to realize that I was not a corporate or professional guy (my father was a Doctor and I always knew that being a doctor, lawyer, or architect was not for me). But, I would be lying if I were to say to anyone that choosing an entrepreneurial life is the “easy thing to do.” Finding balance in your life is going to be challenging (or probably non-existent) and your chances at success are very low. However, if you “feel it,” there is probably no other way to live your life. When I have the chance to talk with young entrepreneurs or people who are thinking of launching their first venture and want some perspective, I’m always obsessed with understanding whether he or she is a real entrepreneur or a “want-a-be entrepreneur.” The real entrepreneur showcases many of the characteristics that I described in this article early in the conversation. They are usually very energetic and display bold opinions, driving you crazy most of the time with their style and attitude. The “want-to-be entrepreneurs” are usually more “normal” people. They are easy to deal with, but sometimes lack those unique survival skills that are needed to succeed in the long, wild, and unstable ride to becoming a successful entrepreneur. I try to persuade them that if they are just “thinking and not feeling” the entrepreneurial journey they should probably do something else.
On the other side, when you are no longer operating any venture full time and simply help or support ventures as I do in my current situation, you have to learn to listen, understand, and help or support a venture, instead of being the person who “makes it happen.” I’m still learning about how to do this in a productive way. I wrote about this when I realized that my company (Vesuvio Ventures) achieved our first decade. It’s not easy, at least for me, and I think that it will be a learning experience for the rest of my professional career (and, as my family and close friends say, there is a serious chance that I will never retire which means that, hopefully, I will keep learning for a long time).
In summary, building or investing in startups is a tough life. You are going to be wrong most of the time. Statistics and real-life experience support that thesis. But in my case, the humbling experience of being wrong so many times in my entrepreneurial journey has provided me with a fascinating opportunity to keep learning and do a better job the next time. If you are lucky, your success rate will be better than your failure rate (at least financially) and you will be able to make a comfortable living doing what you love. I’m grateful for this every day. Despite this, I know that I will continue to be wrong and fail in the future. I know how it feels to fail and I hope to accept failure with a humbling approach and keep learning as I continue my career. As Master Yoda says in The Empire Strikes Back movie, “Do or do not. There is no try. The best teacher failure is.” I will keep doing and learning from failure and enjoying the ride in the meantime.