What I realized after selling two startups in 12 months

Original author: Joe Procopio
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Dedicated to those who recently launched or are planning to launch their business. Joe Prokopio is a serial entrepreneur and in the article talks about planning a startup and how to launch it correctly. Without a rake, too, has not done, but a useful personal experience.


Entrepreneurs do well by figuring out what they are doing wrong and making the right conclusions. Many entrepreneurs do not understand that they can learn both from successes and failures.

A couple of years ago, under favorable conditions, I, almost one after the other, launched the sale of two companies. Below is my story, now I have enough information to evaluate past events.

Eight years ago, in a terrible mood, I entered my friend Robbie’s new office. I advised him on the launch of a new startup related to big data. Every time we met him at different Starbucks coffee shops and talked about the strategy and the results of the implementation of the agreements. Today we met in his new, modest office, as he had just moved to his full-time startup.

Recently, our strategy meetings switched to discussing whether he could take a bunch of sports data that he had, automate content and create sites from this data. I liked these meetings. It was about automation, artificial intelligence, technology, writing and sports - these topics are related to my career steps and free time activities.

But it was on this day that I did not show much enthusiasm. Robbie immediately noticed my mood, so I explained to him in colors that I had just come from perhaps the worst meeting in my life - a meeting whose goal was to complete the financing of the project I had been working on for almost a year. What actually happened was an unbelievable refusal. Months of work, planning and negotiations just evaporated in an hour.

Needless to say, I was shocked and without funding. This did not happen the first time, but this time I was furious, mostly angry with myself. There was a lot of hope for this deal, and I was in a difficult position. In very difficult. In fact, I refused another lucrative contract, so I could personally work on this project, which I really believed in.

Robbie patiently listened to my release from anger, and then told me that he was more and more thinking about the platform for automating the creation of the content I was offering, and he thinks that we should proceed.

My mood changed instantly. “Give me the weekend to decide on the design,” I said.

That is how quickly the windows open when the doors slam.

By Monday, we were in the process of developing, creating what would become a StatSheet network, which would then become Automated Insights — a company that would offer the world's first commercially available platform, Natural Language Generation.

However, in our working agreement I agreed on the right to continue working on a project for which I simply did not receive funding, because I strongly believed in it.

After this, events began to happen faster. I started hiring staff, we closed investment round A and got rid of the accelerator. The rest is foggy. In 2012, we accepted Yahoo Fantasy Football on our platform, and suddenly our content began to reach millions of people weekly. Then came dozens of other customers, including the NFL and the Associated Press. We closed the strategic round B in 2014, the same year our automated content project collected over a billion articles for dozens of customers.

But there was another project.

It was ExitEvent.

ExitEvent - a startup with a data network as a source of information, transformed from an altruistic hobby into a full-fledged second startup by the end of 2011, with 3-5 hours per week that I could spend on it. It gave a lot of money. Almost from the very beginning, there was interest in acquiring and financing ExitEvent, and by mid-2013 I knew that the path we had chosen in Automated Insights was about to eat the meager amount of free time I could spend on ExitEvent.

I also knew that ExitEvent was beginning to suffocate due to the limitations of my time. I knew that the project could turn out to be something more serious, and I knew, although each of my entrepreneur’s instincts was telling me “no,” it was time to drop it.

So I sold ExitEvent American Underground, a regional incubator, and media companies. And less than 12 months after the ExitEvent acquisition was completed, Automated Insights was overbought by Vista Equity Partners.

ExitEvent was my ninth startup, and Automated Insights was the tenth. It was the first time I jumped like a ball between two startups, and this is something that I would never do again, but I got a lot of lessons that really help me with my eleventh startup. It was a small background, and below are directly the lessons that I learned.

Do not follow the playbook

This is the most important thing I can tell you. Do not worry that your startup does not look, does not act, does not talk and does not feel like other startups. Do not create another Facebook, or Coinbase.

And because of the love of everything that is holy for you, do not make your startup work like other startups. None of the startups became successful, because it was based on the same principles of management, development methodology, sales methods, hiring methods or financing plans, like the one that was created before it.

Do not hire staff if you do not need it.

I am constantly amazed at how much can be done these days with fewer resources. For all that, the economy spawned a whole part-time industry in order to satisfy most non-critical needs. Yes, you have to fix an agenda for your leaders, founders and sellers that everything related to operational management, legal, financial, human resources, payment relations can be outsourced.

ExitEvent was, for the most part, mine unlike some great content creators (for example, Automated Insights - approx. Trans.). But I managed this, programmed the site and functionality, promoted to the market, sold, even dragged and poured kegs of beer at our events.

Now not everyone can program, market, sell, and find time to pour beer. But even with these pivotal roles, relationships will always be more important than contracts and promises. If you find all the right people, motivate them and treat them like gold, they will be waiting for a win. If you do not maintain relationships with close people, it can be costly in the future.

Don’t waste money if you don’t need it

You would be shocked by how much money was really spent on Automated Insights. We all received low salaries, we went to a cramped and smelly office with small windows, in the unwanted part of the city, with worn furniture and a broken ping-pong table as our reception. When we had to spend money, we spent wisely. Talented people, tools, research and development, sales and marketing - in that order.

As for ExitEvent, spending on it was mostly from my credit cards.


Another common element between Automated Insights, ExitEvent and every other startup that I created or was part of, is that at some point I started programming. I will be the first to admit that I program with some uncontrollable fury until everything breaks, but these skills were more than necessary.

Learn how to program, but not just learn how to write code. Enter there and build. If you have a vision, you should be able to express it in something other than Powerpoint. If you do not create a technical startup, do not study and do not participate in the technical side of anything that you create. No industry has progressed without progressing. Make these achievements your secret weapon.

Do not raise money until you see a massive influx of customers

Too many times, I see that entrepreneurs are looking for venture capital for start-ups (VCs) that will not get a VC, because VC is not suitable for them. Still not suitable, or maybe not at all. A venture investment or other type of financing that was paid out of my own pocket was never right for ExitEvent. ExitEvent will always be a dash to a double base, and not a home run (in baseball: a player’s run through all bases after a successful strike - comment.). In the end, it ended up much better for me - the owner of 100% of the company.

In Automated Insights, we only attracted investments when we needed to go to the next level and we could show customers and incomes that would lead us there.

Money raised is not free money. Raising money always takes a lot of time, is mentally draining, difficult and creates more problems than real dollars. It will never be easy, no matter how many times you have done it. Remember this.

Don't overdo it when thinking about what you are building.

In ExitEvent, the mantra was "to be different and be better than everything that was before." This mantra was easy to live because she was me. I did not have any committee.

We spent a lot of time talking about what should be Automated Insights, both externally and internally. Many management meetings were devoted to product and company positioning. We dedicated time to the mission of the company, the culture and well-being of those people who donate so much to work for us.

The answer lies in the middle of these approaches to building these two startups.

Slowing down the experimental curve

At the beginning of the startup life cycle, everything is an experiment. You constantly revise what you build, how you build it, even why you build it. As the startup matures, the field for experimentation narrows - you build the product and focus on the feature set.

As you get into the growth cycle, the experiment should slow down to a crawling speed. This happens quickly for most startups when they realize that all these changes actually cause more problems than successes. Before you hit the accelerator, you need to choose a direction.

There are so many things that I wanted to do in both Automated Insights and ExitEvent, from those that I have never had to do, but in which I was 100% sure that they would work. I put them in the background, but never got to the background. It occurs to me that this is why the majority of serial entrepreneurs rarely go too far from the moment the company was founded. They simply did not have time to finish what they started.

There is no such thing as luck

When funding for the first iteration of ExitEvent failed, I saw it as the worst break in my career. When this indirectly led to the creation of Automated Insights, I thought it was one of the damn good steps. I went despite the main pros and cons in both startups, I have amazing memories and regrets from both. And I could tell you, I am happy that they both worked well for me.

But doing it for the tenth time, I would say that there is no luck. There is a commitment, risk, sacrifice, victory, loss, recovery, and passion. Nothing else. Things work as they were intended.

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