Masterminds vs. Happy Hours: Walk Before You Run

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My Guest: Nick Gray is the author of The Two-Hour Cocktail Party and founder of Museum Hack. He's mastered the art of hosting events that strengthen networks and build genuine connections. In this conversation, he shares practical systems for hosting gatherings, why every leader needs a personal website, and lessons learned from his viral blind date trip to Tokyo.

The Learning Leader Show

Two Great Ice Breaker Questions:

1. What's a compliment that someone has given you that you've never forgotten about?
2. If you could teach any class about a topic that you're an expert on, what would it be?

The power of a network is real: As a leader, you're probably hiring people regularly or looking for investors. By hosting simple, lightweight meetups or dinner parties, or happy hours once a quarter, you can strengthen your network, build it, and keep those loose connections or weak ties warm.

Mix professional and personal contacts: For me, a really boring event would be all work people. Look for occupational diversity. If you're hosting a work event, invite some other random folks who you know are gonna be good conversationalists and add to the energy.

Don't reach for the top shelf first. Most important advice for leaders: do not invite your most impressive contact to your very first happy hour or meetup. Your first party should be for your neighbors, the parents of kids at your school, those LinkedIn connections, high school buddies you haven't seen in a while. Your first party should be a comfortable meetup for 15 to 22 people that you host at your home with just cocktails, not a dinner party. Then slowly, once a quarter, you'll be adding more people to it and filtering your list.

Collect RSVPs to ensure attendance. New hosts are absolutely terrified that nobody will arrive. As long as you get a minimum of 15 people to show up, your party will generally be a success. Use platforms like Partiful or Mixily (not Paperless Post or Evite) to get people to RSVP, let them know what to expect, and send reminder messages. Ten days before, send a reminder message hyping up the party. About a week before, send another reminder message with a little dossier of who the attendees are. Write something little: "Ryan Hawk hosts a podcast. He wrote a book. He lives in Ohio. Ask him about the ski trip he went on with his family." This serves to make anxious people or socially awkward feel like they're welcome and they have a conversational access point.

Practical hosting tips on event day: Label your trash cans and your bathrooms. As people arrive, greet and welcome every single person, and make them a name tag. Write it out right in front of them, first name only. Do not pre-write your name tags.

Force collisions through structured activities. Your job as a leader is to go through life collecting the interesting people that you meet and helping them meet each other.

Can you become a connector? One way to be a connector is to host these meetups and force the collisions. Lead two or three rounds of introductions at your meetup. Make a little announcement 30 minutes after it starts: "There are so many interesting people here. I want you all to meet each other. We're gonna split into small groups. It might seem silly, but I promise the purpose tonight is for you to talk to as many new people as possible. We're gonna split into small groups of three or four people, and you're gonna go around and tell your life story in two minutes."

End on time, especially for weekday events: Host from 6:30 to 8:30 PM with a hard stop on Tuesday or Wednesday nights. People appreciate having an end time because they have responsibilities. Having that end time makes them more likely to RSVP yes and actually attend. "I get more compliments on my party ending on time, and they leave with a positive experience, so they want to return for another."

Why every leader needs a personal website. If you have a blue check verified on Instagram, if you post at least once a month on LinkedIn, you probably need your own personal website. It's proactive reputation management. People are out there searching for you on Google and on ChatGPT. It may not happen every single day, but it probably happens every week. Whether it's parents of your kids at school, whether it's new employees, people are googling you. You want to have a personal website to put your best foot forward and make a good impression. Carrd.co to create a simple homepage or cloudflare to set up your domain name.

Keep it simple: You don't need a Gary Vee type page. Your page can look like a Google Doc. Feed these large language models your story and bio. My website is plain text, simple homepage. I used to have a fancy design site. Now I'm like, dude, it doesn't matter. 80% of my visitors are on their cell phone and just want to read some text and have some links.

The tweet from 2024 that changed everything.

The viral Tokyo blind date trip taught me I was ready to share my life with someone. I ended up meeting my wife a couple of months after this experience because I realized I was ready. From a business perspective, one of the most interesting things while that was happening and for about a week afterwards: anyone would accept my phone call. My callbacks were instantaneous. My dial to answer fast. People were reaching out from everywhere. I was like, whoa, is this what it's like to be a celebrity?

"I came back to Texas after the trip, ready to truly settle down and find a relationship and meet my now wife."

Write like you talk: The best book about storytelling is Storyworthy by Matthew Dicks. Don't try to write a LinkedIn post that says "I'm happy to announce." Would you actually say that to someone? No, you wouldn't. Say it like you talk.

Advice on Blind Introductions: Use a double opt-in intro. Reach out to one person first, "Hey, are you taking new clients before I connect you with a friend?" Get both parties' permission, separately - then send the email.

Give yourself a Free Day: Dan Sullivan suggests one free day a quarter from work. Make it a weekday, and even get a burner phone so you can't check your work text/emails, so you're completely disconnected from work.

The keys to being a great host/MC: Priya Parker does such a great job talking about the theory of being a good leader. The host that doesn't do a great job is the one who's too cool to care. Give explicit instructions to people. You are a ring leader for an event, and you're in charge of everyone's energy levels and keeping the show on the road.

Add value before taking value. Never send someone a message, "I'd love to pick your brain," or "I'm looking for a mentor." That is take, take, take. Think about how you can add value first. When you add value first to people, it's some sort of law of reciprocity. They're much more likely to want to help you out or do something in return.

Advice for new grads in the AI era: AI and new tools are eating into the ability for companies to hire low-level employees that do grunt work. Learn how to use the tools themselves. Work with small businesses and entrepreneurs where you can make a difference.

Develop a writing practice: Matthew Dicks has this activity called Homework for Life where every night you write down some note, some anecdote, something that stuck out for you. It gives you ideas about things to write about.

Use AI as an editor, not a writer: Don't outsource your thinking to AI. Use the tools, understand how to use them, but don't outsource your thinking. It'll spit back something decent, but you don't want to outsource your thinking, especially as a leader.

1. Nick says your first party should be for neighbors, school parents, and LinkedIn connections you haven't seen in a while (not your most impressive contacts). Who are 15-20 people in your life that fall into this "comfortable but haven't connected recently" category that you could invite to a simple cocktail party?

2. He emphasizes "add value before you take value" and never says "I'd love to pick your brain." Think about someone you want to connect with. What's one specific way you could add value to them first before asking for anything in return?

3. Nick hosts events once a quarter to keep weak ties warm instead of trying to have individual coffee meetings with everyone. What's one relationship-building activity you're currently doing inefficiently that could be replaced with a group gathering?

#663 - Priya Parker: The Art of Gathering

#545: Will Guidara: Unreasonable Hospitality

#430 - Matthew Dicks: Change Your Life Through The Power Of Storytelling

Audio Timestamps

02:06 Icebreakers and Personal Stories

02:55 The Art of Hosting Events

08:27 Practical Tips for Successful Gatherings

20:16 Mastermind Events and Personal Websites

25:36 The Importance of a Personal Website

26:47 Crafting an Engaging Bio

29:27 The Viral Tokyo Trip

37:04 Living an Interesting Life

41:57 The Art of Hosting and MC'ing

44:50 Advice for New Graduates

46:35 The Power of Writing and Storytelling

49:07 EOPC