I used to be the kind of American who loved a quick New York-style meeting. Walk in, fast intros, distill overlaps, debate for a few minutes, then leave before the latte cools. Limited small talk or pleasantries, just cut to the chase and done.

Then London happened. Fifteen years of pastry breaks and digressions. Meetings here sprawl. Lunch slides into coffee, coffee slides into “just one pint,” and suddenly you’re discussing AI ethics over sticky toffee pudding. It’s about the long game… relationship first, deal second. I got used to breathing room.

Fast-forward to last month in San Diego. I had time between meetings and reached out to someone interesting. No real agenda, just being “friendly”. The guy said “Swing by, I have 15.” I pictured sunshine, tacos, maybe a stroll. Nope… stopwatch on, espresso already half-gone, eye contact set to “prove it.”

Old me would’ve loved the speed. New me tried small talk… a joke about jet lag (not even a chuckle). My sprint reflex was dull. I was running in flip-flops, while this guy slept in a hypobaric chamber (1).

Twelve minutes in, I realized my error and made it clear that I had more to offer him than vice versa. He granted overtime, and at 29 minutes walked out saying he’d see me next time in London (eg he’d love some of my contacts).

Walking out, I wondered, “Did Europe make me soft”?

I texted my friend Jordan about this ‘hardcore’ guy. He had a simple reply:

Not only do I love tea and cakes, I actually write about the glory of a 3-hour conversation. What have I become!?!

I’ve become someone who values relationships, and broadly that’s a good thing. Europe helped me build a different muscle group. Long talks build depth, while short ones force precision. Focus on deadlifts and you’ll struggle with sprints.

The workaround is cross-training. I’ll schedule more time-limited conversations to stay sharp, and continue my marathons to stay human. I’ll use AI to help draft a “power paragraph” – one breath, all value. I’ll relive my debate days by writing five potential objections and a one-line reply for each.

Gear-shifting matters as well. Being able to read the room is a superpower. My goal for the year is to become fluent in identifying both dialects and quickly adapt their cadences – a true dual mastery.

Sprint when the bell rings, stroll when the sun’s out. Come across a stopwatch mentality, then start fast and earn the extension. Or spot pastries and throttle down, then push for a takeaway. Because business (and life) isn’t one speed fits all; it’s the playlist you shuffle on purpose.

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(1) what marathon runners use to mimic high altitude to increase red blood cell production

Yesterday, something magical happened… I managed to have a conversation that lasted longer than 30 minutes. Not just any conversation, mind you, but one that took a glorious 3-hours.

The funny thing is, it didn’t feel like an all-encompassing marathon of ideas, laughter, and brainstorming. There were no grand assertions or emotional embraces. It was just a nice long catchup with someone who I enjoyed being with. It was both special and not that special at the same time (if that’s possible?).

Now, don’t get me wrong, I appreciate the efficiency of the 30-minute coffee catch-up. It’s the happy meal of social interaction: quick, familiar, and gets the job done. But let’s be honest, it’s never as good as the picture. You’re no longer hungry, but not exactly satisfied.

Those 3-hour conversations, though? They’re the Michelin dining of the social world. You savor the conversation like a perfectly cooked dish, the interesting questions the amuse-bouche, the exciting possibilities the main course, and dessert is looking forward to your next catch-up.

So, here’s my ambitious goal: by the end of the year I aim to have more 3-hour conversations than 30-minute catch-ups. (Wish me luck, we’re talking literally swimming pools of black tea!)

I’ll ditch the ” gotta run” mentality and embrace the potential of extended conversation. Instead of asking, “How about we connect next week for 3 hours?” I’ll leave ample time after my normal conversations for overflow. If they’re going well, who knows how long they could last!

Now, if you’ll excuse me, I have some strategizing to do. How do I subtly extend a ‘quick coffee chat’ into a conversation worthy of a three-hour epic? Wish me luck!”

I’ve always noticed speed varies drastically from company to company. Some are amazingly efficient, while others meander (or worse).

Recently, a founder asked me to help significantly increase their company’s speed. After a few conversations, we distilled the issue to focus and accountability. Basically, cut activities that don’t directly create value and stop accepting mediocre results.

I wonder, are focus and accountability the key drivers of speed at any company?

Are there other components of speed I’m missing? Do most companies consider how specifically to increase execution speed?

One aspect may be the mentality of team members; maybe some inherently execute faster and this company just has slow people? Or can anyone be fast when key company and leadership components are in place?

Basically, I’m left with more questions than answers. But I’m pretty confident speed is a leading indicator of a company’s success.

(1) Surprisingly it was a first-time request… seeing as how common the issue is

Here’s one of my favorite slides from the “Going Global” session I hosted today with some amazing ScaleNL Dutch founders.

While some people present what they know, I basically overshare all the things I screwed up over the years… kind of like my version of group therapy.

I remember caring so much about consistency, brand, execution… when none of that really moved the needle compared to trusting and supporting the great people around me.

Hopefully reliving me on the Iron Throne trying to force people way smarter than me to ‘bend the knee’ will help others not make the same mistake 🙂

I love what Stéphane and his crew at OpenVC are building, such an amazingly open ethos. They shared 14 actual cold outreach examples recently sent to VCs, all had the same general cadence:

Hi <VC>, I’m <NAME> with <BACKGROUND> building <PRODUCT> achieving <TRACTION> raising <ROUND>.

Anything feel off to you? Basically, all 14 are totally canned. And these were the best 😐 If you’re a VC, do these ever actually convert?

Email 5 at least writes “we feel like a great fit for <VC>”, but doesn’t qualify why with applicable examples.

Email 11 refers to a “chart on your website”, so at least there was a glance of research, but nothing further?

My guess is the amount of research/commonalities a founder refers to in a cold email directly correlates with their first call conversion rate:

Canned < 1%
Highly targeted > 10%

I wonder how many first calls an email like this would get…

Hi <SPECIFIC VC>

Congrats on closing your fund <#>, I’m sure <INVESTMENT> must have helped – what an amazing company!

I noticed your post <POST> and investments in <Y> and <Z>, we seem to share a common interest in <INDUSTRY/MODEL>. In fact, I’ve been building <COMPANY> to solve <PROBLEM>, which I’m guessing you have some experience with as well…

Whatever else is written from here, as long as it’s concise, my guess is the VC would appreciate the outreach enough have a conversation.

If a founder puts this kind of effort into an investor email, just think what they will do to win customers, staff, etc. (or so a VC might say to themself).

A founder recently asked for my advice about creating hype and FOMO while fundraising, stemming from a post making the rounds in entrepreneur circles. Their take was…

“Based on the article, we should pretty much stop engaging with VC’s at the moment as we’re not (actively) fundraising, that information is a currency, and a certain amount of mystery seems key. Better to disengage entirely for the best chance of success?”

Something didn’t sit right, I better have a peek at this article – is it really suggesting founders not to engage with investors until actively fundraising?

Most of the advice is solid: a ’sherpa’ can help with introductions and navigate discussions, other investors suggesting a ‘hot deal’ creates urgency, craft your story based on current trends, don’t waste your time with tons of investor calls, be creative when attracting interest. Yep, that all resonates.

But this founder (and quite a few others, I’m told) focused on ‘intrigue is an asset’ as a key takeaway. If they plan every interaction, minimize casual interactions, and fill an investor’s mind with good news, then mystery and the magic of ‘limitless potential’ is created. Which then leads fo FOMO and ultimately investment.

In essence, unless you’re in total PR mode when speaking to investors, they’ll find out your company is a complete disaster and never invest in you.

To me, it felt like used car sales tactics more than finding a decade-long business partner and board member. But maybe I’m missing something? Perhaps the combination of planned, formal, mysterious, and good news is indeed the path to creating FOMO and raise a round?

So I called several investor friends (7 in total, all Partners of active VCs) and asked for their take on FOMO and relationships during fundraising. How did they source their best investments? How do they advise founders to fundraise? What % of their deals are FOMO related?

Instead of writing a slick post or creating an ultra-hip tweetstorm, I’m directly passing on the feedback I shared with the founder who initially asked for fundraising advice. It’s a combination of these 7 investor conversations and my personal experience. I hope it helps on your fundraising journey… may the FOMO be with you 🙂

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1) Fundraising is about building a relationship over time, based on genuine/open/honest conversations (eg lines not dots)

2) The goal is finding someone you can spend a decade+ building with, who adds much more value than just money

3) Building investor relationships can have upsides other than fundraising, like introductions to potential revenue/staff/etc

4) Investors have seen it all (startup ups/downs), they see through planned ‘good news’ interactions (eg “the shit comes out in DD”)

5) A too much intrigue can set expectations too high, create trust issues, and even kill a deal that would have gone through

6) Instead of being ‘mysterious,’ think about frequently reaffirming the big vision (1/3) while sharing wins (1/3) and struggles (1/3)

7) Short term FOMO (eg mainly dark until fundraising) does happen in +-25% of rounds, vs 75% based on long term (9+ mo) relationships

8) This kind of FOMO is usually because of serial exited founders, incredible team, insane traction, or significant market change

9) FOMO fundraising can work, but there’s high risk if the market doesn’t form and you’re left with limited relationships to fall back on

10) When a FOMO fundraising ‘works’, it’s hard to push through IC, the dynamic can be off, and there’s limited rapport to work from

11) Optimal rounds are pre-emptive offers (with others then bidding), which entail some kind of dialogue and relationship

12) Treat fundraising like business development by segmenting your list into A) 5-6 top prospects B) 10-20 decent potentials, C) 40+ all other leads

13) ‘Massage’ deeper relationships with an A list YOU choose, vs 20+ surface exchanges with ‘time-wasting’ incoming interest

14) Spend time being top of mind with existing investors, frequent ambassador mentions to your A list go a long way