Hey y’all — just a few days with the right people can change a lot.

I’ve learned that time and time again after running nearly 50 founder retreats over the years, but each time is a unique experience with new lessons.

A few weeks ago I partnered with Tyler Denk (CEO of beehiiv) and his newsletter Big Desk Energy to host 9 founders for a 5-day mastermind in Costa Rica.

We curated a hand-picked group of incredible founders (over $100M in combined annual revenue) to teach each other new things, build stuff, pick apart each other’s strategies, and generally help each other succeed.

(We also surfed, rented a boat, had a private chef all week, and more).

TLDR, it was a vibe. Here’s the recap:

I don’t live in Silicon Valley these days. I’m down in Charleston where, despite being an amazing place to live, you don’t get that same cracked founder energy on a daily basis like you do in SF.

So this retreat got me thinking… why not start bringing together some of that Silicon Valley energy more often like I used to? I’ve already set up the next one:

I’m hosting a 2-day Delegation Mastermind with my friends at Oceans.

We’ll be going deep on the right ways to use OpenClaw, Claude, and how to hire the right AI-fluent operators to give you time back and more leverage to let you grow faster.

The goal of the mastermind is giving you more execution capacity.

Here’s the deets:

Spots are super limited, as we want to keep this to be a highly curated group, so signup here (no obligation).

This retreat had both bootstrapped founders and VC-backed folks (including one from YC).

And from the opening night hot tub conversations to the presentations we each did to teach each other something new, there was a lot to learn and take in.

So I took a couple weeks to digest it all and start implementing some of it in my own business.

Here’s what I brought back with me:

The youngest founder in our group inspired me quite a bit.

He pushed all of us in the group to aim for excellence. His company is in a crowded industry where differentiation is hard, but he’s managed to stand out by taking a counterintuitive approach to just about everything he does, and explicitly making his goal to be the best in the world at it.

A great example of this is cold outbound email.

A lot of people say cold outbound is dying because of the oversaturation of AI spam emails. I get 3-4 per day on a good day.

But one of the founders at the retreat, who used this strategy to get multiple billionaires to reply and become his clients, believes the opposite.

He believes that everyone’s digital footprint has enough breadcrumbs for you to draft hyper-personalized outreach that truly grabs attention… if you’re creative enough with it.

His approach goes against the traditional advice of not wanting to invest too much time and too many resources before knowing if something will be successful. He explicitly ignores this and ha at times spent an entire month proactively building something for a prospective client he hadn’t even contacted yet.

(No surprise: it landed him the deal.)

His thinking is that the traditional approach talks about what you can do, but in a world where anyone can easily do that now, he wants to stand out by showing what he can do.

When it fails, it sucks. But when it succeeds, it’s a big win.

Most people won’t commit 10+ hours of time to something that might not work out. The best founders will.

I had invited my buddy Keith from Lightfield but even though he wasn’t able to make it down, I wanted him to share his story with the crew — it’s inspiring.

After building Tome to 25M users, raising over $81M, and reaching a $300M valuation he and his co-founder decided to pivot.

They realized that LLMs, while being great at drafting first drafts, lacked the deep context necessarily for high-quality finished work on their own.

Their solution was building the data right into the product by creating an AI-native CRM.

But, seriously, imagine telling the investors you recently raised $81M from that actually you weren’t convinced enough your own idea was worth building further.

That must’ve been hard.

But they did it, and Lightfield is awesome. It’s the first CRM I’ve used that feels like I don’t need to do the tedious work at all, it does it for me.

Let’s be honest, LinkedIn is a pretty cringey place.

A public resume of your professional experiences, and a lot of braggy yet vapid content in your feed? Sounds bad.

But three of us at the retreat have over 40,000 followers on LinkedIn, including me.

One of the founders presented his entire LinkedIn strategy, and how it drives tons of inbound business for his startup (including converting over 25% of all outbound cold DMs he sends).

Here’s a way oversimplified version of his process:

He’s used this to grow his business to nearly $10M in annual revenue and his process is very similar to what my team and I do for tons of founders at Megaphone Studio.

If you want to build your own inbound and outbound LinkedIn lead gen engine, book time with me here.

Basically everyone there had used OpenClaw or Claude to build extremely specific, custom agents or software to support niche use cases within their business.

Tbh, I felt behind.

And since I came back it’s basically all I’ve been doing.

It’s let me cancel some of our subscription SaaS tooling, but not all.

And also tbh, would it really be a good use of time to do that?

While you should certainly automate what you can easily, you don’t to sync countless dev cycles into rebuilding everything from scratch just to save a few bucks. That’s a scarcity mindset.

Better to automate the easy things and use that time to invest in growth.

With that said, custom/personal software absolutely is here to stay. Just because the caSaaStrophe of 2026 is somewhat overblown doesn’t mean it isn’t real.

The #1 thing this retreat reminded me of (which was the first I’d done in 2 years) is that if you want to know where things are headed and feel inspired to push yourself harder, whatever you goals may be, there’s no better way to do it than being surrounded by people who are doing it too.

If this looks like a good time to you, join me and Oceans for the next one in San Diego in late May:

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