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1776: A Startup Story
I recently turned the last page of the book ‘1776’ by David McCullough. It’s a fantastic read that I wish I had read sooner. If you haven’t read it yet, I highly recommend picking it up. The narrative of the small, disorganized and messy Colonial Army, outgunned and outmanned, enduring a year of relentless battering,…
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Lessons Learned: Navigating the Stock Market Roller Coaster
I started investing in the stock market during the 2008 market crash. It was a wild time to start looking at stocks. Blue-chip companies were going to zero, 100-year-old brands were trading at hugely depressed levels. It’s easy to sit here in 2023 and know that everything would work out, but at the time, it…
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You Need More Meetings Than You Think
In 2018, after three years of running Snaps, we had to make a difficult pivot in terms of who we were selling our product to. We found that, for our conversational AI product, our buyer in the enterprise was not in marketing as often, but increasingly in Customer Experience and Customer Service. The AI market…
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2023 Predictions
Here are a few things that I believe we could see happen across technology and the broader business market in 2023. To be clear, I’m not making any investing advice! I’m just having some fun thinking about the coming year. Equity markets bottom out: I believe that the public stock market still has more downside…
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What Happened in 2022
When we hit the slower week between Christmas and New Years, one of my personal traditions is reflecting on what happened, and thinking about what could happen next year. For me, the benefit of this exercise is to pick my head up, look around, and try to make sense of the world. Last year as…
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Spoon Bending: FTX, Twitter and Disruptive Founders
“Do not try and bend the spoon, that’s impossible. Instead, only try to realize the truth…there is no spoon. Then you will see it is not the spoon that bends, it is only yourself.” – Spoon boy, the Matrix. There is no reality, there is only your perception of reality. To bend the world to…
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Setting Early Stage Goals
The more time I spend with early stage startups, the more I see CEOs and their leadership vary a lot on how they think about setting goals. Having spent 30+ quarters doing this, I believe I’ve gotten to an effective framework for early stage startups, where pretty much everything is difficult to predict. Often, leaders…
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2022 Predictions
2022 Predictions I’m joining in on the predictions fun, and offering some of my predictions for 2022. I find predictions are most interesting if they have some objective measure associated with them to avoid the “this kind of happened” moment when looking back. I tried to provide predictions with some type of observable, measurable outcome…
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Doubling Down
Having spent the better part of 15 years in and around startups, one thing I’ve observed is that the best entrepreneurs I’ve seen have a tendency to double down where they’re strong, and either ignore or hire around where they’re weak. Example strengths could be vision-casting, product insight, or sales. I’m sure there are others,…
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Narrow AI Everywhere
In technology and startups, there are what I think of as micro-trends and macro-trends. I think of micro-trends as moments when everyone starts an X for Y company. Examples might be Uber for Dogs, AirBnB for cars, etc. They pop up and everyone is wrapped up in them for 15 minutes, and then they sputter…