Thought Leadership Threads

The past 2 years have been brutal to the Startup ecosystem.
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Darwin is back and capital has become less available and more expensive.
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Many startups haven’t gotten “far enough fast enough” and can’t raise the capital they need to survive.
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So it shouldn’t come as a surprise that M&A is a topic that’s coming up more and more frequently in Board rooms as a way of “landing the plane”.
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A few thoughts:

2020 + 2021: Most “valuations relative to traction” were crazy
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2022 + 2023: Bridge rounds helped startups grow into their valuations

Now + 2024: Most “valuations relative to traction” will be reasonable
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But some startups can raise at high multiples due to momentum:🧵👇

AI is undeniably going to change the world but 99% of AI companies will fizzle and die.

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I have real, actionable advice about how to build durable AI companies but understanding my perspective requires a primer on how I think about AI.

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Trust me, you’ll like it: 🧵👇

You’re probably familiar with SAFE notes if you’re an early stage Founder or Investor.

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But did you know that later stage Investors and Founders are also using SAFE notes?

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And have you figured out that later stage SAFEs can create real downstream problems for a startup? 🧵👇

Board meetings can be incredibly awkward when the CEO and one or more of the company’s Board members don’t see eye to eye.

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When I see this happening, I frequently play the role of “peacekeeper” and start by reminding both parties of a well-known parable:

The startup ecosystem is finally seeing good companies come to market again.

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But after a year of focusing on costs and runway, some startups aren’t exciting anymore. Many startups that try to raise will hear: “We want more proof!”

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Here’s what you need to know about proof:🧵👇

At a startup, stock options can be lucrative depending on the success of the company.

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With valuations down, Founders are asking to reprice historical options.

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Here’s what it means, why it’s important and when it’s appropriate.

MANY startups are living with bad decisions they made when cheap capital flowed freely.

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Massive value destruction was driven by Founders playing Hungry Hungry Hippo, trying to accumulate as much revenue as possible.

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A few thoughts on how to learn from their mistakes:🧵👇

Startups that have clean narratives and “up-and-to-the-right” results can generally raise capital with minimal friction.

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But a fundraise takes on an entirely different form when a startup has “asterisks” that complicate the story.

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Unfortunately, asterisks are now the norm!🧵👇