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Master the Art of Graceful Endings

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October 2, 2025
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Master the Art of Graceful Endings
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A few decades ago, when I was raising funding for a startup, I made a lasting impression on an investor by not only talking about how successful we would be but also highlighting what would happen if we weren’t. Later, in an informal setting, I asked him what had persuaded him to invest in us. He told me that during the pitch, I mentioned, “And if all our predictions and expectations are wrong, we will use the last of our funding for a magnificent farewell dinner for all our investors. You’ll have lost your money, but at least you’ll get a great evening for it in return.”

I don’t recall this being part of the original pitch or my strategy. I probably just blurted it out to break the ice, but it impressed the investor. He told me it was refreshing to speak to an entrepreneur who wasn’t blinded by his own pitch. The fact that I had a scenario ready for both success and failure told him that I was honest and realistic.

Now, the startup did not succeed, but we still had a nice, opulent dinner with the investors at the end— and we did them one better. As soon as we realized our predictions and expectations were wrong, we offered two options: struggle and pivot or return what was left of our funding to our investors. We chose option two, and so did they, so everyone got some money back (about 40% of what they had invested) plus a lovely evening with excellent food and drinks. When we raised money for another startup a few years later, almost all of them signed up in our first round.

Obviously, I would have preferred to make this startup successful instead, but I still regard it as a successful endeavor. I gave it a try and had a plan ready when my experiment didn’t work out, and in the process, I built relationships that outlasted that one startup.

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In a unique start to his ruling against President Donald Trump’s administration on September 30, U.S. District Court Judge William Young included a scanned handwritten note sent to his office. The note read: “Trump has pardons and tanks – what do you have?” At the top of Young’s opinion in AAUP v. Rubio, which ruled that Trump’s effort to deport foreign-born student protesters was unconstitutional.

October 8, 2025

As you may know, The Next Web, the company I founded in 2006, is nearing the end of its lifecycle. The events and media business is being wound down, and only TNW Spaces will continue. TNW Programs was sold off a while ago and will also continue. There won’t be another TNW Conference, and soon there won’t be new articles on the site; people are losing their jobs, including me. It’s a painful process, but I guess I’m taking it well because it feels natural and logical. When we sold TNW to The Financial Times in 2019, we were very ambitious and optimistic, and surely I would have liked for the company and brand to outlive me. However, when the business struggled, I also felt very comfortable with the company ending graciously.

When you’re reading a good book, there’s a moment near the end when you start reading slower because you don’t want it to end. I love those moments, as they signify that it’s been a great experience. But then you know that good stories need good endings. So, this is the ending of a great story that I’ve enjoyed participating in.

I’ll keep writing, but this will be my last official TNW story. I’d love it if you would subscribe to my writing over at Substack. It will be less tech-focused, more unpredictable, but just as insightful as before.

Boris, out.

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