While we've seen massive advancement in the power of AI tools over the last year or so, we're clearly still just in the early innings of this shift. Reading through the tea leaves of Joanne Stern's interview with Apple software chief Craig Federighi and marketing head Greg Joswiak, I was actually a little hopeful.

It feels like Apple hopes Siri will evolve into a highly reliable and integrated AI companion, deeply embedded across its operating systems rather than functioning as a standalone chatbot. It's something that feels like Apple is uniquely suited to do given continued consumer loyalty to its hardware and operating system. They have unparalleled ecosystem control (iPhone, Watch, AirPods, Mac), on-device intelligence, user trust, and deep OS integration.

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There’s no single secret to great deal flow—but the best investors treat sourcing like a craft, not a lottery. They combine consistency, curiosity, and community to ensure, not hope, that they’re seeing the best deals.

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A lot of founders ask, “What are the metrics for a Series A?”

“You don’t earn a fundraising round as a reward for the past.”

What you’re doing is selling a ticket to the future—and the thing you’re trying to convince an investor is that you’re a) presenting a vision of the future they want to be a part of and b) you can actually execute on it.

That latter part is where we need to talk about tadpoles and frogs.

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This week, I got my wisdom teeth out—all four of them.

You might be wondering what took me so long. I’m 45 and most people have them out between the ages of 17 and 25.

One helpful bit of context is that until very recently, I hadn’t been to the dentist since 1998.

Here’s what happened…

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Your venture career is better off if you're working alongside the best possible people. The more of them there are that perform up to the kind of level where they have a shot at bringing in a fund-returning deal, the better it is for you. 

Remember, when, at best, only about 20% of firms ever make it to a Fund III, there’s more of a chance that your path to partnership is blocked by the death of your firm than by the presence of another investor in your way.

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In 2015, a then 18-year-old Harry Stebbings launched The Twenty Minute VC from his bedroom in London. No background in venture capital. No industry connections. No podcasting experience. Just a cheap mic, an internet connection, and two things:

Curiosity and initiative.

Instead of waiting for the perfect job, a mentor, or an MBA to unlock those doors, he just started asking questions. Literally.

He cold-emailed VCs and invited them on his podcast.

Not to pitch them. Not to impress them. Just to learn from them.

And here’s the thing: they said yes. Not all of them, obviously—but a few. Guy Kawasaki and Brad Feld were early big names, but why did they bother?

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Gone are the days of the startup launch party. Remember those nights of trying to explain to a Techcrunch reporter why your app was going to change the world over thumping music and bad venue WiFi? 

RIP.

Most startups know not to blow a bunch of money on a big party before they have their first users, but legitimate questions remain about what you do in its place—and how you open yourself up to the world that gets attention. 

Founders still want to get press and investors to notice them, but they don’t have a lot of money to work with. What are they supposed to do today?

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VCs don’t owe you a goddamn thing—and especially not after they’ve already met with you. That was the time they had for you. They offered a meeting—no more and no less.

The fact that you didn’t spend the last few minutes of the meeting asking for specific feedback and posing the question of whether or not the VC was going to move this forward as a champion of the deal or at least whether they wanted to schedule a next call is your failure. When you’ve got any kind of a lead—be it for selling your product or selling your equity—and you let them go with no scheduled next step, you risk never speaking to them again.

That’s your problem, not theirs.

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