This is going to be BIG.

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But There's So Much Content Out There!

This is going to be BIG.

I’m very lucky. I know a lot of really smart, interesting people. That’s why I find myself telling a lot of people that I’d love it if they shared their thoughts more often in public. I don’t much care whether they do it in writing, or a newsletter, a podcast or on LinkedIn—but I feel like I every time I interact with them, I learn something or I’m inspired to think about things in a different way.

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The BSList: You're Raising the Wrong Amount (No. 93)

This is going to be BIG.

“How much should I ask for?” Almost every single time I talk to a founder as they’re prepping their raise, this comes up—and it’s absolutely the wrong way to think about a round. The right question is, “How much do you need?” When you raise money, the way you should build up your ask—ideally—is the following: “We need X amount to get to Y milestone, which we can do based on Z assumption in the model—which we’ve already proven.

pitching 357
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The BS List - We Don't Like This Space (No. 52)

This is going to be BIG.

One of my favorite startups to have backed was a travel company called Noken. You answered a few basic questions about travel preferences, like pace, the fanciness of the hotel, etc., and then BOOM they sent you a link to an app with your whole trip, completely booked, with a map driven itinerary and a text concierge available to make last minute changes, etc.

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The BSList - Busted Cap Table (No. 104)

This is going to be BIG.

Recently got the following question: “I’m getting inbound from investors and have a screwed up cap table because of my venture studio relationship… I don’t really know what I should and shouldn’t say but I feel like when I mention how much I own, but when anyone shows real interest we get to a point where I can tell they are turned off by the cap table that I haven’t had any control over.

VC 195
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Why Don't More Emerging VCs Have Coaches?

This is going to be BIG.

Being a VC means not only honing your skills as a judge of character, assessor of business models, and calculator of risk, but it’s also a lot of difficult interpersonal communications, narrative creation, and long-term goal setting and positioning. While some of the hard skills and prerequisites to do the job can be taught by those around you with more experience, the latter activities often have to be figured out in a way that is extremely tailored to you as an individual—so it’s just not goin

education 195
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This is Going to Be. Not on Substack

This is going to be BIG.

Almost 20 years ago, sometime after Fred Wilson started writing and just before Brad Feld jumped in, I started “blogging”. I put that in quotes because no one really calls it blogging anymore and there aren’t even that many people still doing it from those days. A few went pro and most just moved on to other platforms, including Medium and Substack.

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Why AI Won't Be the Investment Opportunity Everyone Thinks It Is

This is going to be BIG.

The other day, I was watching an episode of Seinfeld and was struck by how dramatically different location-aware mobile phones have made our day-to-day existence. The entire plot was based around no one having a phone in their pocket. Watching the characters leave answering machine messages for people (and miss them), use paper maps, and get lost on the way to a cabin made it all seem pretty dated.