Landing Meetings In Silicon Valley

My cold email playbook for landing 15 meetings in one week

I'm back! You might have noticed I've been a bit quiet lately—I've been super focused on building Marloo, my new company, and repurposing this blog as a living document of our journey and tactical advice. Last year, I was lucky to spend time with Substack founder Hamish McKenzie, who helped me coin the term ‘starting a startup backwards’ to describe our unconventional approach. We're tackling a really interesting challenge for our customers with a fantastic team and investors on board. We're not quite ready for the big reveal, but I'll keep you all in the loop!

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Since 2015, my regular trips to the Bay Area have been driven by a focus on building impactful relationships—and I've found that strategic cold outreach to be a powerful tool.

On my most recent trip, I sent 35 cold messages and received 17 responses which led to 15 meetings in one week with exceptional founders, operators, and investors.

I firmly believe in proactively creating connections, and on these trips, I've dedicated significant time and energy to crafting effective cold outreach

This outreach has sparked connections and conversations that have generated new ideas, thought patterns, and friendships—and I'm better for it.

Crafting effective cold outreach is an art form. It requires the ability to grab the recipient's attention, demonstrate your value, and make a clear ask.

Here are a few tips and tricks I’ve picked up along the way.

Be selective and targeted

Spend a disproportionate amount of time curating a list of people for cold outreach prior to every trip. My search vectors centre around:

1. Founders and experts building in similar areas to me

2. Investors who have recently backed specific companies I find interesting

3. Fellow Australians and New Zealanders who live in the Bay Area (the shared cultural context often leads to quicker connections and a higher likelihood of a response).

You can leverage LinkedIn, Twitter and Substack to find great folks. I keep track of people using a personal CRM.

Guess emails if you cannot find them openly (just make sure to put the guesses under ‘bcc’). I also use Twitter DMs and LinkedIn messages with good success.

Demonstrate something interesting

What have you built or done that makes you unique and stand out? You want to channel this into the opening of your outreach in a punchy and succinct way.

Examples;

- I founded company A, we do B, and have raised from firm C. 

- I was the first employee at A, I led growth and we acquired 1m users.

- I represented my country in sport A and won B national titles.

Also, bonus points for a crafty subject line. On a recent trip I used “Robinhood of New Zealand” as the subject to highlight my experience at Sharesies and had multiple people state it was an interesting hook.

Show you’ve done research

I tailor each email to the recipient and make sure to include something that shows I’ve invested time learning about that person.

Examples;

- I saw you invested in company X

- I listened to your recent podcast with Y

- I noticed you led growth at company Z

Have a clear ask

You need to be clear about what you want from this person. Be direct and punchy! Anything else is a waste of time.

Examples;

I saw your experience at <big venture capital firm>, I'm really curious to know:

- What is the most interesting early-stage company you've seen recently and why?

- What problem are you most excited about that no one is building for?

Given you founded <billion dollar company>, can you talk me through:

- How you found your first paying customers

- What you learned from early go-to-market experiments

Do not ask for a meeting outright! If you’re emailing the best thing to do is say “Happy to chat live or async via email”. If you nail the clear ask, most of the time you’ll be offered a meeting.

Add value

Think of something you are uniquely positioned to teach someone about. Regardless of whether you end up actually doing this, it demonstrates willingness to help. This is the social currency that the Bay Area is built upon.

An offer I always make is “happy to share insights from VC in Australia & New Zealand. I’ve invested in a number of companies & funds like X and Y”.

Timing is everything

Your best chance to send messages is on Tuesday the week before you arrive in the Bay Area. That way you can say, “Hey, I’m in town next week”.

For anyone who hasn’t responded by the week of your visit, I send a follow-up when I land saying ““Appreciate you’re busy! Bumping this to the top of your inbox. I’m around SF until Friday”. Don’t follow up more than twice as there is a fine line between persistence and annoyance.

Allow flexibility and overflow in your calendar for last minute meetings to be scheduled. On my last trip I received a reply at 7am asking if I was available to meet at 9am that same day.

Prepare for rejection

Many people won’t reply and that’s perfectly okay. The reason you’re doing this is the small chance that someone replies and starts a conversation. You never know where it will lead.

Getting a meeting is 10% of the work

In 2015, cold outreach led to me meeting a super impressive person at Meta, who invited me to their office for breakfast. Pretty cool right?

I had naively assumed I’d get a tour, take some photos and go home. Instead we sat down and all they asked was ‘what do you want, why are you here?’. I hadn't prepared properly and completely fumbled.

While social capital goes a long way, everyone in the Bay Area is building something important and has scarce time.

Start any conversation with your purpose for meeting and always be prepared with three leading questions.

I recently recounted this story to them—nine years later—and we both reflected on how valuable that early lesson was.

Please subscribe if you find this content valuable. I’ll be writing more as we build Marloo 🚀