I’m staring at a blank subject line again. It’s a Tuesday morning, coffee going cold beside me, and I’m about to send email number forty-nine. Forty-nine months in a row. Nearly five years of consistent, intentional outreach to my community as director of the UC Irvine ANTrepreneur Center, and not once have I run out of things to say.
What I don’t usually mention is that when I sent the very first one, there were eight people on that list.
Eight.
That was my entire crew at the time.
The people who knew what I was building and believed in it enough to want updates. And now, as I hover over send on email forty-nine, there are over a thousand people subscribed to that newsletter. I didn’t grow it overnight. I grew it one person at a time, one email at a time, one genuine relationship at a time.
People ask me all the time how I’ve grown my LinkedIn network past twenty thousand connections, or how I’ve built a social media following of over three hundred thousand collectively across platforms. They expect some kind of elaborate strategy. A funnel. A system. A secret weapon. The truth is almost embarrassingly simple: I just keep in touch.
That’s it. That’s the whole thing. But staying in touch, really staying in touch, in a way that builds trust and not just a contact list, takes more than good intentions. It takes a framework. And years ago, at some conference I can no longer name, I heard someone talk about a simple approach to staying connected, specifically in the context of fundraising and advancement. I don’t remember who said it. But it stuck with me, and I’ve been using it ever since. I call them the Three I’s. I can’t take credit for the idea. But I can vouch for the results.
Before I get into the framework, let me back up. Because it only makes sense once you understand why having a crew matters in the first place.
Why a Crew Changes Everything
Think about some of the most famous expeditions in history.
Think about some of the most famous expeditions in history. Captain Cook charting the Pacific. The first ascent of Everest. The Apollo moon landings. None of them were a one-person show.
None of them were a one-person show. They had a captain, yes, but also navigators, engineers, people to maintain the ship, people to manage the provisions, people whose sole job was to make sure the vessel kept moving. The crew wasn’t a luxury. The crew was the mission.
Not everyone has that kind of operation, though. Maybe you’re a solo founder, an individual contributor, someone building something real without a team behind you yet. And that’s okay, because some of the most legendary voyages in history were made by solo sailors too. People who set out alone, navigated by instinct and grit, and made it across open water on their own terms. There’s something deeply admirable about that. I get it. I’ve done my share of solo sailing.
But here’s what every great solo sailor has in common with every great expedition crew: people back home.
The shipwright who built the hull. The navigator who helped chart the course before departure. The investor who funded the voyage. The mentor who had already crossed those waters and lived to talk about it. Whether you’re running a fleet or sailing single-handed, you have people in your corner who made the journey possible.
That’s your crew. And your crew isn’t just your team. It’s your mentors, your investors, your advisors, your colleagues, the person who grabbed coffee with you two years ago and said something that completely changed how you think. It’s anyone who has ever helped you move from where you were to where you needed to be.
And here’s something worth saying plainly: investment doesn’t always mean money. When someone gives you their time, their advice, their belief, their referral, they are investing in you. Those people deserve to stay in the loop. They deserve to know the ship is still moving.
Research from the U.S. Small Business Administration found that businesses with active mentoring relationships see significantly higher revenue and growth rates. A separate analysis found that seventy-five percent of entrepreneurs who had ongoing mentoring relationships increased their revenue. Seventy-five percent. That’s not a coincidence. That’s the crew doing its job.
The problem isn’t that leaders don’t know they need people. They do. The problem is they don’t know how to keep those people close once they’ve found them.
Why Most Crews Drift Apart
Here’s what actually happens. You meet someone incredible at a conference. There’s a real conversation. A genuine connection. You both say let’s definitely stay in touch, and then you don’t. Months go by. Then a year. And by the time you think about reaching out, it feels awkward. Like you missed your window. Like reaching out now means you must need something, and you’re embarrassed by that, so you don’t do it at all.
This isn’t laziness. It’s the absence of a reason to reach out.
Most people only contact someone when they need something. And that pattern trains your network to associate your name with a request. That’s not a crew. That’s a transaction. And no ship gets very far running on transactions alone.
The Center for Creative Leadership puts it plainly: the quality of your relationships directly shapes the quality of your leadership. Not the quantity. The quality. And quality requires consistency. Your crew doesn’t stay your crew just because you once shared a good conversation. Ships need maintenance. So do relationships.
The Three I’s: How to Keep Your Crew Close
This is the framework I first heard in the context of fundraising, and it translates to every kind of relationship worth keeping. Whether you’re staying connected to an investor, a mentor, a potential collaborator, or the colleague two levels above you who took a chance on introducing you to the right person, this gives you a genuine reason to reach out without feeling like you’re asking for something.
I use it for my newsletter. I use it for one-on-one outreach. And honestly, when I’m staring at a blank social media post and have no idea what to share, I run through these same three questions. What’s something informative I can share? What’s something my audience would find genuinely interesting? Or is there something I can invite them to? It cuts through the noise every single time.
Every time you reach out, lead with one of these three things.
Informative. Send them something useful. This could be an article, a stat, a trend in their industry, a resource, an opportunity, a piece of news that’s directly relevant to what they’re working on. The key word is relevant. You’re not blasting generic content into someone’s inbox.
You’re saying I thought of you when I saw this, and the specificity of what you send proves it. My monthly newsletter is a good example. It’s not a broad lifestyle update. It’s a specific, targeted dispatch for people who are genuinely invested in what’s happening at the UC Irvine ANTrepreneur Center, undergraduate entrepreneurship, our students, our programs, and the ecosystem around it.
The people on that list are there because they care about that world. So that’s exactly what I give them. Information they can actually use. When you show up as someone who consistently delivers value, you become someone worth hearing from. That’s a reputation that compounds over time, and it keeps your name top of mind before you ever need a favor.
Interesting
Show them you pay attention. This one is more personal. You’re not sharing something useful in a professional sense. You’re sharing something you know they’ll genuinely find fascinating, because you actually remembered what they care about. Maybe they mentioned at that conference that they’re into vintage maps. You spot one in a bookstore and send a photo. Maybe they told you they’re learning to sail, and you come across a documentary about solo circumnavigation. You send it with two lines and no agenda. That’s the message that stands out.
Not because it’s impressive. Because it’s personal.
Robin Dunbar, the Oxford anthropologist behind Dunbar’s Number, found that humans can meaningfully maintain around one hundred and fifty relationships, but only when those relationships involve regular, genuine interaction. Interesting outreach is one of the most underrated ways to keep a relationship warm without a formal agenda. It signals that you were thinking about someone even when you didn’t need anything from them. That’s what crew members do. They think about each other.
Invitation
Give them a reason to show up. This is the most powerful of the three, and also the most underused. But I want to be clear: an invitation doesn’t have to be a physical event. It can be an invitation to anything you’ve created or curated. Invite someone to read your latest article. Invite them to watch a talk you gave. Invite them to a workshop, a webinar, a book you wrote, a community you’re building.
For me, that might mean inviting someone to check out one of my four TEDx talks, or to learn more about my keynotes, or to pick up a copy of SpeakerSHIP or my newest book EntrepreneurSHIP, or to explore the workshops I run both on land and at sea. The invitation is simply saying: here is something I made, and I think it’s worth your time. That kind of invitation elevates people. It makes them feel chosen, not marketed to. And it creates the kind of shared experience, even a virtual or asynchronous one, that deepens a connection in a way a cold message never could.
When I host events at the ANTrepreneur Center, I’m always thinking about who in my network would genuinely light up in that environment. Not who I should invite. Who would belong there. That distinction, intentional versus obligatory, is felt on the receiving end every time. An invitation says: I built something, and I want you to be part of it. That’s what you tell a crew member. That’s how you keep them aboard.
Tend to Your SHIP
I started with eight people on my newsletter list. Eight people who cared enough to say yes, keep me posted. That was enough. That was everything. Because the point was never to have a big list. The point was to show up consistently for the people who were already paying attention.
Whether you have one person on your crew or a hundred, the strategy is the same. You don’t need a massive network to start. You just need to start. Pick one person today. Be informative, be interesting, or send an invitation. That’s it. One message. One connection kept warm. Forty-nine months later, that’s how you end up with over a thousand people who genuinely want to hear from you.
Here’s what I know to be true: your leadership is a direct reflection of the people around you. The mentors who challenged you before you were ready to be challenged. The investors who believed in the ship before the hull was finished. The colleagues who stayed on deck when the storm hit. None of those relationships maintain themselves. You have to tend to them. Consistently. Intentionally. Not just when you need something.
So the next time you’re staring at a blank message window, or a blank social media post, not sure if you should reach out or what you’d even say, ask yourself one question: can I be informative, interesting, or invite them to something? The answer is almost always yes.
Hit send.
Your crew is out there.
They just need to hear from you.