Introduction

S2 E2 – Even Leaders Need a Tribe: The Power of Peers

S2 E3 – An Event Networking Guide (for Introverts)

S2 E4 – Ditch the Pitch: How to Craft the Perfect Introduction with Clay Hebert

S2 E6 – Reaching the Unreachable: Befriending Celebrities, Business Leaders, and Billionaires

S2 E8 – Becoming a Catalyst: How to Host Dinners & Unique Live Experiences

S2 E13 – How to Learn from Mentors Instead of Mistakes

S2 E15 – Prioritizing Relationships

S2 E16 – The Six Ways to Invest in Relationships

About the Authors

Jayson Gaignard 

Jayson Gaignard is the founder of MMT, one of the world’s most exclusive communities for entrepreneurs. He’s an expert relationship-builder, one of Forbes “Top Networkers to Watch,” and the author of Mastermind Dinners: Build Lifelong Relationships by Connecting Experts, Influencers, and Linchpins.

His work has been featured in Entrepreneur Magazine, Forbes, Business Insider, and in best-selling books like Tim Ferriss’ Tools of Titans, Todd Herman's The Alter Ego Effect, Dan Martell's Buy Back Your Time and more. 

You can learn more about Jayson at jaysongaignard.com.

Mateo Chaney-Martinez

Mateo Chaney-Martinez is an aspiring entrepreneur and community-builder with a background in career coaching. He loves helping high achievers expand their impact through relationship-building and opportunity creation.

After spending 2023 in Madrid, Spain and Bangalore, India, he moved to a founder’s house near Boston, MA, where he currently resides.

You can learn more about Mateo at mateocm.com.

Invest in People Like You Would in a Business 

If there’s a single lesson to be learned from this guide, it’s that you should invest in people like you might invest in a business, because amazing people become increasingly amazing over time.

This is the low-hanging fruit of relationship building, so it’s baffling that no one talks about it.

Think of yourself as a talent scout. The earlier you invest in someone, the more valuable that investment is to them, and the more impact you have in their life. Plus, like any good investor knows, an early investment in a successful company provides the highest returns.

Collect Relationship Intelligence

If you’re going to invest in people, you must do so by adding value. This requires knowing where someone is at and determining what they may need.

You do this by capturing relationship intelligence, which includes anything and everything unique to the people you want to connect with. You might capture dreams, quirks, goals, obstacles, strengths, areas of expertise, and even information on who and what they care about.

Collecting this information makes investment opportunities clear.

The more you know about someone, the easier it is to create highly personalized touchpoints, showing them they are seen, valued, and appreciated.

If you start paying attention, you’ll realize people constantly share relationship intelligence. In fact, people share so much information that it’s impossible to hold all the details in your head.

To combat this, the best relationship-builders create PRMs—CRMs for personal relationships—to store and organize all this information. These systems make investing in relationships easier. It may be worthwhile to start your own.

The 6 Ways to Invest in Relationships

Now that you’re collecting relationship intelligence, it’s time to use that intel for good.

Here are six ways you can invest in your relationships.

Investment #1: Provide Resources

The most obvious way to invest in someone is to provide resources.

Whether you recommend articles, make introductions, or provide capital, your goal should be to help them get where they want to go faster.

Developing a personal balance sheet featuring your strengths, weaknesses, and areas of expertise may reveal unique resources you can provide.

And don’t underestimate the power of being resourceful. A willingness to figure things out can unlock many doors, especially if you’re young and eager to learn.

Investment #2: Be Their Biggest Fan!

The most successful people constantly push to the edge of their comfort zones. This is courageous, but also deeply vulnerable. Helping in those fragile moments can be very impactful.

If you know someone’s goals, consider their potential fears. Then try to find ways to curb their risks, worries, and doubts.

Sometimes investing at the right time is more valuable than investing a huge amount.

Investment #3: Thoughtful Gifting

If you’re capturing relationship intelligence, you may find opportunities to give a thoughtful gift.

Done well, this can be very impactful. But be careful! Poor gift-giving has negative outcomes. As Jayson frequently reminds people, “You’re actually better off giving no gift than a poor one.”

If you want to learn more about gift-giving, listen to Jayson’s full episode on the topic: “Corporate Gift Giving: 3 Reasons You’re Doing It Wrong.”

Investment #4: Gratitude

Writer William Arthur Ward once said, “Feeling gratitude and not expressing it is like wrapping a present and not giving it.” Anytime you feel thankful for someone, share your gratitude.

Everyone has a deep desire to feel significant and be reminded that what they do matters. Gratitude provides opportunities to show this.

Expressing gratitude can be especially meaningful for authors. They often spend countless hours building a book but rarely hear from people who have benefited and achieved results. If you’ve been impact by a writer, reach out, tell your story, and express thanks!

Investment #5: Invest Indirectly Through Their Inner Circle

Tony Robbins says, “If you want to influence someone, figure out who already influences them.”

This same idea can be applied to relationship-building: If you want to care for someone, figure out who and what they already care about.

Thoughtful investments in someone’s inner circle can show extreme care.

Investment #6: The Follow-Up

People often get this investment wrong because they don’t take the time to personalize it.

If you meet someone and want to pursue deeper relationship, see if you can provide support with your follow up. The best way is to help with their specific needs, using the above strategies.

When doing this, you’ll want to avoid asking “How can I help you?” because, while well-intentioned, it creates more work for them. Suddenly they have to figure out how you can help.

Even if you’re ever at an absolute loss for how to help, say “if there’s any way I can support you, please let me know.” This offers your help without requiring them to find something.

And no matter what kind of follow-up you send, don’t send the message if its content wouldn’t be worth a phone call. Meaningless messages hurt relationships more than they help them.

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Next-Level Relationship Building

Once you’ve established a strong relationship base, the key becomes subtraction, not addition.

We can only maintain active relationships with 150 people, known as Dunbar’s number, so being intentional about who we spend our time with remains essential as our networks expand.

Jayson says he goes wide with his networking and narrow with his nurturing.

This episode focuses on the former, exploring how to organize your network. The next episode explores the latter, sharing ways to pour into your relationships.

But before we discuss organizing our relationships, we must dispel some misconceptions.

The 5 Relationship-Building Misconceptions

Misconception #1: Prioritize Relationships Based on People’s Success

The best way to build a world-class network is by prioritizing world-class people.

This doesn’t mean prioritizing those who are most successful, but rather those who are most dedicated to growth. Choose to see someone’s potential over their current accomplishments.

If you do this, you’ll watch those amazing people become increasingly amazing over time.

Misconception #2: Create a Tribe Like You

Surrounding yourself with similar people may be comfortable, but it’s rarely transformative.

The strongest networks are full of people who challenge you. You may have different strengths, divergent skills, or even disagree on fundamental issues. But you also care deeply for one another, provide unexpected insights, and encourage growth.

As Jayson says, “if everyone is thinking alike, then somebody probably isn’t thinking.”

Misconception #3: Relationships Are Forever

From true love to BFFs, we’ve somehow absorbed the idea that relationships are meant to last. But in reality, life brings change. Some people really are in life for a reason or a season.

Instead of measuring relationships by length, value them by the growth they’ve prompted.

Misconception #4: Prioritizing Relationships Means Writing People Off

In the relationship-building world, you want to avoid burning bridges at all costs.
Life is unpredictable and people will surprise you, so it’s wise to be nice to everyone.

If you absolutely must disassociate from someone, lead with compassion, empathy, and forgiveness. As a rule of thumb, Jayson often waits 24 hours before sending tense emails.

You never know if you’ll run into someone and you don’t want there to be bad blood.

Misconception #5: Relationships Die If Not Maintained

This misconception goes hand-in-hand with our belief that relationships are forever. Life changes inevitably leave us with thousands of relationships that could be rekindled and become strong ties. Researcher Adam Grant calls these people you used to know “dormant ties.”

The beauty of prioritizing relationships is that no decision needs to be permanent. You can always change plans and prioritize different relationships based on your wants and needs.

Jayson’s Relationship Prioritization Framework

While everyone prioritizes relationships differently, Jayson’s strategy provides valuable lessons.

Visually, his framework looks like a series of expanding concentric circles, like a target. The first layer, core, is the bullseye, and each successive layer is a ring around it.

Here’s each layer explained:

The Bullseye: Core

The first circle is full of the most important people in your life. These are the people who truly have your back and would never let you go hungry or sleep on the street.

If you’re just starting with relationship-building, begin by developing a strong core.

And even if you already have a robust network, prioritize this circle. You never realize how much you need these relationships until you suddenly do.

Ring #1: Connectors

Jayson’s next circle is made up of the people who know everybody. He always says that “access is the ultimate asset” and connectors are the best way to get disproportionate levels of access.

To identify connectors, start by looking backwards. Who is responsible for many of your best relationships? Those people are likely connectors.

Ring #2: Community

After connectors, Jayson’s third circle is community. This is your tribe, the group of people you’d likely consider your friends.

It can be helpful to fill your community with an even mix of mentors, peers, and mentees.

Mentors help you look to the next level, calling you into growth.
Peers keep you accountable at your current stage, walking through challenges with you.
Mentees provide perspective, reminding you how far you’ve come.

Filling your community with all three helps you meet your needs and serve others.

Ring #3: Friendly

The three C’s—Core, Connectors, and Community—put Jayson at 150 people.

After reaching Dunbar’s number, Jayson has two additional circles: Friendly and Fringe.

Friendly includes people with whom he has a positive relationship. If he can ask for an introduction without overstepping, the person is probably in the ‘friendly’ category.

Jayson frequently builds goodwill in these relationships through mastermind dinners and micro-interactions, like texting them a book recommendation.

Ring #4: Fringe

Fringe is the final layer of Jayson’s relationship framework.

These are people Jayson’s friends know, even if he doesn’t know them personally. They’re your 2^nd degree connections on LinkedIn.

To tap into your fringe layer, Jayson advises reaching out to your network whenever you need help. There’s a lot of power in sharing your needs and letting others offer introductions or solutions. And if you’ve been deliberate to plant seeds of goodwill, people will be happy to help.

The world isn’t always about “who you know,” but also “who knows you.”

Relationship-Building Consistency

If you’re serious about maintaining relationships, it can be helpful to develop deliberate practices for strengthening bonds.

These routines ensure you keep pouring into relationships even when life is hectic.

A few of Jayson’s practices include:

• Booking 1+ hour on Sunday to schedule emails.
• Dedicating time to add information to his personal CRMs.
• Hosting mastermind dinners at least once every two months (often when traveling).

Whether you copy his practices or develop your own, creating routines for relationship management is key to sustaining a strong, positive, and healthy network.

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Why Mentorship?

No matter your field, interests, or life-stage, mentorship is the fast pass to growth.

As Oscar Wilde put it, “Good judgement comes from experience and a lot of that comes from bad judgement.”

Mentors let you learn from the experience of others rather than suffer your own bad judgement.

The Best Mentors

Steven Spielberg said, “The delicate balance of mentoring someone is not creating them in your own image but giving them the opportunity to create themselves."

The best mentors recognize this.

Rather than tell you what to do, they ask questions, offer various perspectives, and tell personal stories instead of giving direct advice.

The 6 Myths of Mentorship

Myth #1: Mentorship is a one-way relationship

Mentorship is not just the mentee learning from the mentor. The relationship goes both ways.

Mentees provide mentors with a sense of significance and can also offer “reverse mentorship.”

Reverse mentorship might include:

• Bringing energy
• Explaining modern trends
• Providing distinct perspectives
• Demonstrating new technology

Myth #2: Mentors are hard to get

The opposite is actually true: it’s harder to find a good mentee than a good mentor.

Our instant-gratification culture heightens young people’s distractibility, leaving them unfocused. Contrasting this culture will help you excel, and making it easier to get a mentor.

Myth #3: You need to find the “perfect” mentor

All successful people reach their success by prioritizing some things over others. That requires sacrifice. And since it’s implausible that anyone has made the exact sacrifices you want to make in every area of life, the perfect mentor likely doesn’t exist.

Instead of seeking a perfect mentor, build a network of mentors with different areas of expertise.

Myth #4: Mentors are for amateurs and people just starting out

There will always be people ahead of you throughout life, especially in distinct domains. You’ll continue to benefit from mentors as you grow in different areas of life.

If you keep seeking mentorship, you’ll keep finding mentors. You just have to look.

Myth #5: Mentorship needs to be long-term, time-consuming, and face-to-face

Mentorship can take a wide variety of forms, depending on the needs of mentor and mentee.

For example, entrepreneur Derek Sivers has been mentored by people who don’t even know he exists. He asks himself what one of his “mentors” would say whenever he faces a dilemma, and since he’s read enough of their work to know how they think, he often reaches a solution.

Myth #6: Mentorship and Coaching are the same

Coaches are good at helping you think through things, but they don’t need firsthand experience.

Mentors have been there, done that, and can show you how to do something.

Both relationships are valuable, but they serve different purposes.

The 4 Stages of Successful Mentor/Mentee Relationships

Stage #1: Self-Assessment

The first step in finding a mentor is evaluating yourself.

First, ask if you’re a good fit for mentorship:

• Do you have a growth mindset?
• Would others want to mentor you?
• Would you want to mentor you?

Once you feel ready for mentorship, it’s important to assess your goals.

Where are you now? Where do you want to be?

Contrasting a clear vision with a current self-analysis reveals upcoming challenges. These challenges will point to the people you want as mentors.

Communicating relationship objectives also help secure mentor buy-in.

Stage #2: Matching

Once you know what you’re trying to accomplish and which challenges you’ll face, it’s time to create a “hot list” of potential mentors.

Don’t just target people at the “top.” It’s crowded up there, and thus harder to get mentorship.

Instead, try asking this question:

• If I’m unable to reach this person, are there alternative people who could help me reach the same outcome?

For example, it might be a lot easier to reach a bronze medalist, even though they were just marginally worse than the gold medalist.

It’s often more helpful to find mentors who are 2-3 steps ahead anyway, since they clearly remember your current stage and have good advice.

(One exception: people miles ahead can see the big picture. They might be able to help you avoid unnecessary detours on your road to success.)

Once you have this “hot list,” begin reaching out.

Cold outreach can be scary, but there’s almost no risk compared to the very high rewards.

Stage #3: Exploration

The next stage of mentorship is highly individual, based on your personal relationship, but here are a few high-level tips.

First, start small.

Your initial outreach can be as little as asking a nuanced question based on an article they wrote or thanking them for how one of their teachings impacted your life. Little interactions like this can increase mentor buy-in without requiring major commitments. Then you can go deeper and make bigger requests as the relationship progresses.

Second, be prepared to put in the work.

Many mentors test mentees by assigning work and seeing if they go above and beyond. Jayson recommends spending two to three times as much time preparing as you do meeting. This might include reviewing meeting notes, completing action steps, and formulating good questions.

Putting in the extra time shows your dedication to and appreciation for their mentorship, which helps the relationship grow and thrive.

Third, if your mentor is comfortable, record your conversations.

This way you can go back and catch any details you missed, while also focusing on making your mentor feel heard by asking clarifying questions. Sometimes you’ll disagree with feedback when you first hear it but come to agree with it the second or third time around.

Stage #4: Closure and Reimagining

If a mentorship isn’t working out, communicate that. (But don’t burn bridges!)

Sometimes you’ll accomplish the goals you had when you began the mentorship. If so, take the opportunity to celebrate, then evaluate appropriate next steps.

If you do end a mentorship, be sure to honor the relationship by continuing to help your mentor.

This might include:

• Sending relevant articles and resources their way.
• Introducing them to people who they may enjoy meeting.
• Sharing stories of how their mentorship helped you (both privately and in public).

You should also send the elevator back down, by mentoring others.

Final Thought: Mentorship as Data

One final thought related to mentorship comes from Aristotle. He said, “It is the mark of an educated mind to be able to entertain a thought without accepting it.”

Mentorship—and any insight it provides—should be seen as data.

Listen to it. Consider it. Mull it over.

But ultimately, you decide what to take and implement.

Further Reading:

If you want more information on mentorship, including outreach scripts and troubleshooting tips, check out The Definitive Guide to Mentoring by Todd Herman. It’s a short guide like this one—his is 30 pages—specifically focused on mentorship.

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Why Become a Catalyst?

Before you start hosting events, it’s important to understand why they’re worthwhile.

For attendees, connecting with people they wanted to connect with is extremely valuable.

In fact, Thornton May built a nine-figure business by inviting Fortune 500 CIOs to group dinners. While these CIOs were previously isolated, the dinners enabled them to meet each other and talk through the challenges their companies faced, crowdsourcing solutions. Occasionally, amidst discussion, they turned to Thornton to ask if his company could help them solve particular problems, too. Thornton paid for the dinners, but everyone won from the interactions.

For hosts, events provide additional benefits, including a boost in status.

In most rooms, the highest-status person gets the most attention. But this also works in reverse. Being the host means you get attention, and that attention makes you seem high-status.

Hosting events also provides credibility by association. By coordinating, you spend time around high-status people and spending time with high-status people makes you also seem high-status.

You can then leverage this boost in status to interact with more accomplished people.

The 5 Dinner-Hosting Ws: Who, What, When, Where, and Why

Why are You Hosting Dinners?

Your dinner-hosting strategy will depend on what you hope to get from hosting dinners.

Do you want to build a network of peers? What about potential mentors? Do you want to use your dinners to increase organizational sales? Or will your dinners be about giving back, connecting people at the early stages of their journey?

Developing clarity around your “why” will instruct every element of “what” and “how.”

If you’re going to host dinners, start by getting clear on your “why.”

What Size Should the Dinner Be?

Now that you know your goals, pick a dinner size that reflects them.

Large dinners are great for building trust and rapport at scale. They enable micro-interactions with every attendee, helping you plant seeds and decide where you want to invest further.

The downside of large dinners is that the host must play facilitator. Instead of being fully present, you’ll have to mingle, sparking conversations and making sure everyone is engaged. This scales with group size, too. As Jayson warns, “The larger the group, the more energy you'll be investing to make sure everyone is having a great time."

While small dinners don’t plant seeds with as many people, the smaller size produces intimacy. Attendees are more likely to open up and be vulnerable, which creates stronger relationships. These small dinners also tend to self-facilitate, making it easier to fully engage as the host.

Pick your size based on what you think will work best. If you don’t like how it goes, you can always try a different dinner size later. The key is to start—you’ll get better at this as you go.

Who Do I Invite?

Dinners live and die by the quality of your curation. Start with your dinner-hosting goals, then look for people who would want to meet each other.

The best strategy is to target an uncommon commonality: what will everyone in the group have in common that they are unlikely to have in common with a random stranger? 

While all relationships must go through the same stages of intimacy-building, this process happens much faster when there is an uncommon commonality. As Jayson says, “The deeper the uncommon commonality, the deeper the bond.”

But be careful! Inviting direct competitors may hurt the dinner’s potential for intimacy.

Where Should I Host?

There are many factors to consider when selecting a dinner location. Here are four big ones:

Accessibility - Consider factors like distance, traffic, parking, and public transit when picking a venue. “Your job as a host,” Jayson says, “is to design an incredible experience for your guests from start to finish, so take time to consider how easily accessible a venue is in advance."

Value - Your best bet is to host at a restaurant with 3.5+ stars. You’ll also want to avoid any restaurants that are overpriced or pretentious.

Dietary Restrictions - Pick a restaurant with a wide array of options, or at the least the ability to accommodate allergies and dietary restrictions. Mexican food is often an excellent choice.

Intimacy – While 4 to 6 person dinners can be hosted almost anywhere, large dinners may require private or semi-private dining. If you opt for private dining, be sure to negotiate with the restaurant in advance. You’ll want to order off the main menu (rather than the pre-fixed one) and avoid food minimums if you can. Sometimes Jayson will suggest ordering a slew of options with the ability to share, giving the impression of variety at a lower cost.

When Should I Host?

The timing of your dinner should be shaped by who you’re inviting.

Consider the lifestyles of your guests, then pick a day and time where they are likely available. You might even opt for breakfast or lunch if that better suits your guests.

Conferences can be especially good times to host a dinner. These events unite similar people and often provide attendee lists, making it easy to find and invite guests. And, by catching people outside their typical schedules, invitees are more likely to say “yes.”

How to Host a Dinner

What follows is a step-by-step guide for hosting dinners. It stands alone and is everything you need to start hosting your own events. But if you want additional support, like exact invite scripts and more, they can be found in Jayson Gaignard’s 2015 book Mastermind Dinners.

Step #1: Schedule Dinner & Book the Restaurant

Once you’ve decided to host a dinner, schedule it and book the restaurant. Adding the event to your calendar makes it real and reserving a table pushes you to execute.

Step #2: Find & Review Invitees

Thinking about your dinner-hosting-why, begin looking for invitees.

Start by tapping into your network, asking if they have any suggestions.

Then try asking, “If I’m notable in this city, where can I be found?” This may lead you to local business organizations or past award winners.

And if you’re still not finding enough people, you might try co-hosting with a local connector—someone who already knows lots of people in the city.

Jayson also tracks interesting people. Anytime he finds someone intriguing on social media, he adds them to a CRM. This gives him an endless list of people to meet when in new cities, which is helpful when hosting dinners on the road.

Step #3: Invitations

Since dinners live and die by the quality of your curation, you’ll want to handpick your guests.

There are two main strategies to securing commitment:

First, you can work up the chain. Start with the person most likely to say “yes” and work up from there. This builds confidence and momentum at the same time.

Second, you can secure an anchor tenant. If you get a “yes” from the most impressive guest, their attendance will make it much easier to recruit the other invitees.

Even if you secure an anchor tenant, you’ll want to be careful with name-dropping. Jayson recommends sharing achievements, like “attendees include a New York Times bestselling author, etc.” without mentioning anyone by name.

Once you invite people, track their status so you know who’s coming, pending, or unavailable.

And don’t panic if you receive early rejections. Invitations get easier as you develop a reputation. Jayson’s first dinner had a 10% conversion rate; now his invites convert 95% of the time.

Step #4: Post-Acceptance, Pre-Dinner

Once a guest commits to attending, you’ll want to send them a calendar invite and intake form. The former locks your event in their calendar while the latter streamlines all dinner-related info. Intake forms are the best way to learn about dietary restrictions, capture details for seating and introductions, and even receive nominations for future dinner guests.

A day before the dinner, you’ll want to send a reminder email to ensure no conflicts have arisen. You can also share some of the group’s achievements to heighten anticipation.

Then, on the day of the dinner itself, Jayson recommends texting every guest from your personal cellphone. This is a nice personal touch and makes communication easy if anyone runs late.

Step #5: The Dinner

Arrive Early & Greet Guests

You’ll want to arrive at the venue at least an hour before the dinner starts. This time helps you get comfortable, meet the servers, pick your table, and lay out name cards for seating.

When guests start arriving, you’ll want to greet as many of them as possible at the door. Greeting guests immediately eliminates the nerves of walking into a new situation.

Starting The Dinner

Once all guests have arrived, start the dinner with some opening remarks. Share the approximate dinner duration and available menu items, before reiterating why you’re hosting the dinner. You’ll also want to remind everyone there’s no soliciting: what happens at dinner stays at dinner.

After these remarks you’ll want to introduce your guests one-by-one. Use this as a chance to brag on all your attendees, highlighting their accomplishments and mentioning commonalities. Your goal is to help people feel safe, allowing space for vulnerability. If natural, you might even lead with vulnerability yourself.

From there, it’s time to let conversation flow. (But snag a group picture once food arrives!)

Wrapping The Dinner

As people finish their entrées, you’ll want to start wrapping the dinner.

Jayson does this by asking everyone the champagne question: “If we were to meet a year from today, with a bottle of champagne, what would we be celebrating?”

Answering this question gives each guest an insight into one another’s goals, often sparking post-dinner follow-ups. If possible, Jayson recommends recording everyone’s answers, too.

After everyone answers the champagne question, Jayson says the dinner is officially over. He tells guests they can leave but are also welcome to stay and keep chatting if they want.

And with that, voilà, you’ll have hosted your first dinner.

Step #6: Post-Dinner

The day after hosting a dinner, Jayson recommends sending a post-dinner thank you.

You can make some comments about the dinner itself, share the group photo, and reiterate everyone’s champagne question answers. If everyone is comfortable, you can also share group emails. This thank you also offers a final chance to request nominations for a future dinner.

If you particularly liked someone, you can go deeper post-dinner. Invite them for a one-on-one or send them a literal bottle of champagne if you hear they accomplish their stated goal.

Dinners are often the seed. Keep pouring into the relationship to help it grow.

Who Pays for Dinner?

The final dinner-hosting question comes at the end of the meal: who pays?

There are several valid options. Choose whichever you think is best!

Option #1: The Host(s)

Jayson always pays when he hosts dinners. He feels it’s his responsibility as the host.

Whether you feel this way or not, paying for dinner also builds reciprocity, strengthening your bond with each guest.

Co-hosting can also help lower costs since you both split the bill.

Option #2: Guests

If you want your guests to pay for their meal, you can let them know by calling the dinner a “Dutch treat” in your initial invite or by creating an Eventbrite page so they can pay in advance.

Option #3: Company Sponsor

Depending on your guests, a company may be willing to cover the bill. This can be a fantastic win-win, since the company gets exposure with target individuals, and the guests get a free meal.

Option #4: Games

One final way to pay is with games.

You can play credit card roulette, letting the server pull credit cards until one remains. Or you can play phone stack, with everyone placing their phones on the table, agreeing that the first person who touches theirs will cover the meal.

These games are great opportunities to increase playfulness and ignite people’s competitive drives, leading to a lot of fun. Just be sure to let people opt out and pay for their own meal if that’s their preference.

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Warning: This Journey Has No Promise of Success

Reaching the unreachable is difficult, far more art than science. You may do everything “right,” even for a long time, and still have nothing to show for it.

But sometimes reaching that one person is worth it. This section gives you tools to try.

Connect with Big Names by Cutting Through the Noise

If you want to connect with big names, you have to cut through the noise. Your contact must stand out from all other requests, and the bigger the name, the harder the task.

Keep this in mind when choosing who to reach and how to reach them.

The Power of Asking

The first step in connecting with big names is getting out of your own way.

Most people defeat themselves before getting started. And even those who try rarely play all-out.

In the digital age, getting your message in front of someone is easier than ever. But doing the work required to elicit a response remains just as difficult. As Jayson reminds people, “The success of your outreach is often in direct proportion to the amount of effort you put into it.”

Use Skills to Open Doors Money Cannot

One effective way to reach the ultra-successful is solving a pressing need for free.

This requires several steps.

First, identify their needs. Do some online digging to find the status of their current projects. Then brainstorm some challenges they may need to overcome, along with how you could help.

Second, reach out with a clear value proposition. Show you did your research, make a clear offer, and be sure to communicate you’ll do the work for free, with no strings attached.

Third, supply social proof. Include examples of past work to show your competence and ability. (And if you don’t have any past work to showcase, see the next section on trading up the chain.)

Fourth, overdeliver. Do everything in your power to wow them with your contributions. The more extraordinary your contribution, the more opportunities you’ll get in the future.

Trade Up the Chain with Social Proof

Reaching the unreachable is rarely the first step in any process. In fact, landing a dream opportunity without the requisite preparedness is likely to produce a bad first impression.

Instead of starting at the top, do free work for smaller organizations. These opportunities help you practice your skills and, if the work is done well, provide credibility for bigger projects.

They also help you practice the outreach process.

For example, you might start with a business in your local community, move to helping a larger organization, support a rising star, and only then start reaching out to the best in a field.

By that point you’ll have the social proof to land the opportunity and the expertise to do it well.

Help Successful People Achieve Significance

Another way to reach the unreachable is by helping them achieve significance.

Everyone wants to feel like what they do matters, especially those who are already successful.

It’s as Zig Ziglar said, “We go from survival to sustainability, sustainability to success, and success to significance.”

Consider how you can help a ‘success’ feel significant.

Has your life been impacted by their work? Tell a specific story about the difference they made.
Have you shared their ideas with others? Talk about what made their ideas so captivating. 

The key lesson is that you can’t contact people just for the sake of reaching them. There has to be some sort of value-add—even if it’s just an expression of gratitude—without a covert contract.

To again quote Zig Ziglar, “You can get anything you want in life if you help enough people get what they want.”

Working with Gatekeepers

Very successful people are often surrounded by a team: spouse, assistant, even chauffeur.

Get to know these people. Not only can they help you get access, but they tend to be quite interesting. You’ll also get a lot further if you consider these people allies, not opponents.

Riffing on Tony Robbins, Jayson says, “If you want to influence someone, influence those who already influence them.” There are few better places to start than with their team.

Beyond someone’s immediate team, there’s also value in exploring their charity.

There’s an expression that “the way to a man’s heart is through his stomach.” Well, the way to a wealthy person’s heart is often through their charity. In fact, you may be able to trade a donation for access to someone’s time.

It’s also worth reiterating the value of being memorable and cutting through the noise.

Jayson sometimes does this by mailing LCD cards, which are physical cards with a little screen on which you can upload a video.

While successful people receive thousands of emails and hundreds of letters, they may never have seen an LCD card before. If you get them curious, you might get them hooked.

Turning Rejection into Opportunity

If you reach out to successful people, you’re going to get rejections. Worse, you might not hear back at all. It’s how the game works: you shoot lots of thoughtful shots in the hopes that a couple transform your life.

But sometimes you can turn those “failures” into successes.

Here’s how:

No Response

Before you do any outreach, get an email open tracker. As the name suggests, this software reveals when someone receives and opens your email, which helps you determine next steps.

If your email was never opened, you know your message wasn’t seen. Try a different subject line and send the email again.

If you can confirm that someone opened your email, you have two main strategies: either restructure and resend the email with a little more information or send the original email again.

Persistence pays, especially with busy, successful people.

Rejection

In cold outreach, any response is a win. Celebrate your “no” accordingly.

Jayson recommends two strategies to turn a “no” into a “yes.”

First, never accept a “no” from someone who cannot give you a “yes.” If a gatekeeper shuts you down, keep looking for another way in. You may get a “yes” when you hit the right person.

Second, if you get to the person you want to reach, ask them, “Under what circumstances would you say ‘yes’?”

Not only does this question get them problem-solving on your behalf, but sometimes it reveals a small concession that completely changes their mind.

Know Your Competitive Advantage

To connect with successful people, you must be worth connecting with. You can do this by being promising, and thus worthy of investment, or fascinating, and thus worthy of intrigue.

For example, Jayson has a friend who has been to 126 countries. Jayson can seat him next to anyone, from millionaires to movie stars, because he knows they’ll find him captivating.

If you’re not sure what makes you worth connecting with, consider developing a personal balance sheet. This should capture your strengths and weaknesses, areas of interest and ignorance, and even ways you can be of service. If you can, enlist the help of friends to get a more well-rounded perspective.

Once you’ve identified your strengths and weaknesses, improve the latter enough that they don’t get you in trouble, then double-down on your strengths. Success comes from exceptionality in a few areas, not well-roundedness across all areas.

And always remember this insight from Jayson’s friend, Michael Fishman: “Credibility can be established with credentials or being transparent that you have no credentials."

Avoid Bad First Impressions

When meeting famous, highly accomplished people, it can be tempting to ask for a picture.

DO NOT DO THIS! You might get the quick photo, but by putting them on a pedestal you kill any chance of a reciprocal long-term relationship.

Instead, try to come alongside them as a peer. Build on an idea they’ve shared or thoughtfully suggest a way they can improve.

When you do this, do it kindly. Studies show that, when meeting new people, we evaluate their warmth first and competence second. 

In other words, “Can I trust you?” always comes before “Can I respect you?”

Be kind and you’ll communicate warmth. Be insightful and you’ll communicate competence.

And remember, no photos!

As Jayson says, “It’s better to make no impression than a bad first impression.”

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The average person gets asked, “What do you do?” three times per day.

That’s over 1,000 times per year!

If the question is so common, it’s worth developing a good answer. Yet most people never do.

This is for two reasons.

First, most people are never taught how to introduce themselves. It’s hard to be good at something you never learn.

Second, if we do get taught, it’s often in the form of an elevator pitch. But everyone hates those—they feel clunky, awkward, and contrived.

Despite never learning how to introduce ourselves, a few pervasive myths hurt our introductions.

The 3 Myths of Introductions

Myth #1: Introductions Should Be 100% Complete

While we all feel pressure to include everything in an introduction, you shouldn’t.

It’s an introduction, not a biography.

If your introduction is “complete,” it won’t be interesting. It’s far better to reveal new layers over time, as you get to know someone.

Myth #2: Introductions Should Be About You

It’s natural to talk about yourself during an introduction.

We all know the basic details: I studied here, I work there, etc.
But the best introductions aren’t about yourself; they’re about the people you help.

Good intros frame how you add value to the world instead of which groups you belong to.

Myth #3: Introductions Should Be 100% Accurate

A third temptation is to include every detail of what you do in an introduction.

I mean, they did ask, didn’t they?

Instead of sharing a ton of details, keep your introduction short. This helps them latch onto the most important information, prepares them to ask questions, and launches a conversation.

Introduction Frameworks

With these myths out of the way, it’s time to create your own introduction.

There are two common strategies:

Strategy #1: Transformation Story

The first introduction goes like this:

I help + [the group you serve] + [what you help them achieve or become]

For example, Clay Hebert says, “I help entrepreneurs fund their dreams.”

And he does—he’s been the mastermind behind hundreds of successful Kickstarter campaigns.

So, what about you? Who do you serve? What do you help them achieve or become?

Draft a few options and see what feels natural, but don’t feel pressure to perfect one. We’ll talk about refining introductions in a moment.

Strategy #2: Introduction by Analogy

The second introduction follows a different formula: I’m [X] for [Y].

For example, a career coach might say, “I’m a personal trainer for your brain.”

Like the first strategy, this introduction isn’t complete. But it does prompt questions.

In fact, prompting questions is the hallmark of a good first line. It gets the conversation going and allows you to expand on your initial introduction. And if you answer these questions by telling client success stories, a good conversation can even bring in new business.

By the way, this works for companies, too.

Varun Puri, Co-Founder of Yoodli, once told me, “We’re Grammarly for speech.” After just one line, I bet you have a guess about what they do—and several questions about how they do it.

Refining Your Intro

Once you have the first iteration of your opening line, start practicing it. Pay special attention to how people respond. Are they confused? Distracted? Curious? Excited?

Use this feedback to tweak your introduction, perpetually improving it over time.

As you improve, remember there’s no such thing as a “perfect” introduction. No matter how good your opening line gets, you’ll still adjust it based on who you’re meeting.

Closing Thought

As Clay Hebert says, we know the question that’s going to be on the test for the rest of our lives.

People will always ask, “So, what do you do?”

Use these tools to craft introductions that spark good conversations and great relationships.

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Why Attend Events?

Events provide high-growth people with an unfair-advantage: speed.

First, there’s the speed of growth. Events are golden opportunities to surround yourself with people a couple steps ahead of you. Befriending these people can reshape your peer group, enriching your life and accelerating your progress.

Second, there’s the speed of wisdom. Learning from panelists and participants can help you avoid costly mistakes, shaving years off your learning curve.

Third, there’s the speed of relationships. Jayson says, “access is the ultimate asset,” and most access comes from your relationships. Events are great for relationship-building with likeminded people, especially since they tend to attract people with uncommon commonalities. These are exactly what they sound like: things people have in common that they are unlikely to share with a random stranger. Uncommon commonalities help relationships get deeper much faster.

These three elements—the speed of growth, wisdom, and relationships—make events high value. In fact, Jayson says, “If you’re not seeing an ROI from events, then you’re either attending the wrong events or not leveraging them to their full potential.”

Let’s take a peek at how to make the most of events.
 

The Event Playbook 

Most event attendees primarily focus on the event itself. This is a mistake!

The majority of event value comes from the pre- and post-event work you do.

This is so important that Jayson dedicates 40% of his energy to pre-event prep, 20% to the event itself, and another 40% to post-event follow-ups.

Use the following playbook to prioritize pre- and post-event work and get the most out of events.

Pre-Event

The 3 Things You’ll Do at Every Event

No matter what type of event you attend, you will always do three things: 1) introduce yourself, 2) tell your story, and 3) make small talk.

Thankfully, you can prepare for all of them in advance.

Introductions are so important that they get their own episode. See S2 E4 for more.

Telling your story is an extension of your introduction. You want to be intriguing, compelling, and always leave people wanting to know more. Jayson prepares a few variations of his story, helping him adjust to time constraints and speak to the interests of specific audiences.

Small talk is the social lubricant between introductions and meaningful conversation. Your goal is to find an uncommon commonality, and when you do, move past small talk by geeking out.

Small talk also becomes easier if you have a few prepared questions in your back pocket. One of Jayson’s favorites is “Have you met anyone who really impressed you so far?” since it gets conversation going and helps him scan for other people to meet.

Pre-Event Research

Once you’re ready for the things you’ll do at every event, it’s time to start preparing for the specific event you’ll be attending.

Look through the speaker and attendee lists, identifying people you want to meet. Pick these people because you find them fascinating, not because you think they’re famous.

Once you have a shortlist of potential connections, poke around their LinkedIn profiles, blogs, and personal websites. Try to find uncommon commonalities or potential conversation starters.

You’ll want to enter the event with low expectations—Jayson aims for good conversations with 3-8 people—so don’t make your shortlist so long that you can’t remember people’s details.

It can also be helpful to make personal decisions, like what to wear and where to eat, before arriving. This helps you avoid decision fatigue and remain fully present throughout the event.

Now with shortlist and potential conversation topics in hand, you’re ready to attend the event.

During the Event

Warming Up

When you arrive at an event, start by getting comfortable.

The easiest way to do this is strike up an early, low-stakes conversation with someone you already know or who looks friendly. The goal here is to relax and settle any nerves.

It can also be helpful to change your body language. Physiology controls psychology, so changing the way you carry yourself will change how you feel internally.

Positive body language also improves first impressions, helping your relationships start right.

In Good Conversations

Once you settle into the event you’ll likely end up in good conversations.

When you do, try shifting into the question-asker role. This has three benefits:

First, asking questions takes the pressure off, since it’s always easier to ask than to answer. Second, asking questions makes people feel good, since everyone likes talking about themselves. Third, asking questions lets you steer the conversation, helping you learn interesting information.

When asking questions, Jayson looks for four things:

1. Who and what do they care about?
2. What are they good at?
3. What are their goals?
4. What obstacles are in the way of their goals?

To learn the last two things, Jayson has two questions he asks back-to-back:

First, there’s the champagne question: “If we were to meet a year from today, with a bottle of champagne, what would we be celebrating?”

Second, there’s the obstacles question: “If that’s your goal, what challenges will you need to overcome to get there?”

Asking those two questions in succession leads people to share what they’re working on and where they might need help, which you can potentially provide.

While it’s important to record insights like these for later relationship-building, try to never pull out your phone in the middle of a conversation.

Relationships move at the speed of vulnerability and few things kill intimacy like a cellphone.
 

Graciously Escaping Conversations

If you talk to many people at an event, you’ll inevitably have conversations you want to leave.

Graciously exiting these conversations is one of the most difficult aspects of events. You want to strike a careful balance between treating everyone kindly while also protecting your time.

Jayson suggests two strategies for graciously escaping these conversations.

First, he recommends “having a small bladder.” Stepping away to use the restroom is always a viable way to leave a conversation. And you can also use the break to record notes on who you’ve met and what you’ve learned.

Second, Jayson sometimes asks people if they’re sticking around for a while. If they are, you can offer to reconnect later and politely slip out of the conversation.

Whether you use either of these strategies or create your own, remember to be gentle. Good relationship builders treat everyone with importance, regardless of their status or background.

Connecting with Speakers

At some events you’ll want to connect with speakers along with attendees. This is completely achievable, but you’ll need to be strategic.

One way to connect with a speaker is by having a micro-interaction before the event. For example, you could send a brief email saying you’re excited to see them speak. If they reply, you can then mention the email when you meet, making you memorable.

You can also engage speakers by talking to them before their presentation. Few people pay attention to them in those moments, so you might get a nice one-on-one conversation.

A third strategy is writing a letter and handing it to the speaker at the event. This lets you to pre-package your message, bypass the competition for their time, and stand out. Honestly, how many other letters is a speaker going to get at an event anyway?

The best strategy to engage speakers, however, is by becoming a catalyst and hosting small events around the large event. We’ll explore how to do this in S2 E8.

Regardless of how you engage a speaker, avoid meeting them right after their talk. Everyone else tries to engage the speaker at this precise moment, making a lasting impression difficult.

Post-Event

To get the most value from events, your work continues after the event is over. Follow-ups are the key to staying connected and building further relationship.

There are four stages of post-event follow-up.

Stage #1: Capture

The first step is transferring all the intel you gathered during the event into a CRM. We’ll talk about how to use this intel to deepen relationships in S2 E16, but the first step is capturing it.

Stage #2: Capitalize

Once you’ve captured everything you learned at an event, it’s time to decide which relationships merit further investment. You can only pour into so many relationships, so it’s important to prioritize the ones that matter most.

When following up with these individuals, you’ll want to do four things:

First, mention something discussed in your conversation. This helps people distinguish you from all the other people they met at the event.

Second, reiterate the goal they’re working towards. This is likely their answer to the champagne question. Including it shows you were listening while giving them a chance to change or expand their answer, giving you more intel.

Third, provide the names of any resources you mentioned in conversation. Whether they came up randomly or in-response to a specific need or obstacle this person is facing, writing these resources down will help the other person find them.

Fourth, if you want, you can make a call-to-action, like scheduling a 1-on-1 conversation. While this can be a good way to deepen relationships, Jayson usually omits a call-to-action. Instead, he leaves the email as a “planted seed.” If Jayson follows up later—maybe even years later—he replies to the same email thread to remind this person of their past interaction.

Additionally, if there was someone you wanted to meet at the event but didn’t, you can still use follow-ups to plant a seed for future interaction. Send them an email saying you’d hoped to meet at the event, and while it didn’t happen, you’re hopeful to meet them in the near future.

One final note: don’t feel like you need to send follow-ups immediately after the event. Sending them a couple weeks later can help your messages stand out from chaotic post-event catch-up.

Stage #3: Close the Loop

If a person you met complimented someone else you know, it can be fun to pass along the compliment. Doing so makes everyone look and feel good while also giving you another touchpoint with each individual. Just make sure you never exaggerate their words! You never know if the person who gave the compliment will get cc’ed back into the email chain.

Stage #4: Check-In

After post-event follow-up, you’ll want to check-in periodically with the people you met.

Instead of sending the dreaded, “Hey, how are you?” emails follow-up with specifics. Ask about the vacation they were looking forward to or congratulate them on an achievement you saw.

A good rule of thumb for follow-ups is to ask if you’d call to say the same thing.

If yes, send the message. If no, don’t waste anyone’s time.

Final Thoughts

At the end of the day, events are about planting seeds. You want to spark relationships with interesting people so you can follow-up and deepen relationships later.

This should frame what events you choose to attend. Pick your events based on their potential for high-quality connections, not just high-quality content.

If you can afford it, it might also be worth paying for intimate, high-price events. Pricing often separates “talkers” from “players,” making these exclusive events extremely high value.

Now you know all you need to get the most out of events. Go have fun!

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Community shapes every aspect of life, from politics to goals and even personality.

John Wooden wasn’t kidding when he said, “Show me your friends and I’ll show you your future.”

The quality of our community even shapes the quantity of our days. 

The Harvard Study of Adult Development, which tracked 268 people for nearly 80 years had clear results 

First, “good relationships keep us happier and healthier, period.” 

Second, loneliness kills, impacting mortality as much as smoking 15 cigarettes a day.

Third, it’s not about the number of friends, but the quality of those relationships. As one of the researchers wrote, “The people who were the most satisfied in their relationships at age 50 were the healthiest (mentally and physically) at age 80.” 

The Current State of Community

If community is so important, how are we doing?

The answer: not very good.

Loneliness is a national health epidemic in the United States, with one in two U.S. adults living with measurable levels of loneliness. The rest of the developed world isn’t doing much better.

Even emails reveal our desire for connection: The most effective subject line—with open rates around 90%—was “You Are Not Alone,” regardless of product being sold.

Social media hasn’t helped, either.

As Jayson put it, “we are drowning in contacts but absolutely starving for community.”

This isn’t working. We need to do something.

How’s Your Community?

If community shapes our lives, it’s worth auditing the quality of our own relationships.

Look at your calendar and social media for the past year. Who do you spend the most time with?

Identify these five people and evaluate them on a scale of 1 to 10 in the following categories:

• Health
• Wealth
• Happiness
• Relationship with Self
• Relationships with Others

Once you’ve scored everyone, add the numbers together and divide by five.

This is likely your personal baseline.

Are you happy with those numbers? Or do you want to make them better?

Consider a Tribe Upgrade

If you want to improve your life, it’s important to surround yourself with the right people.

Here are a few ideas to consider:

Are Your Relationships Past- or Future-Oriented?

When debating a tribe upgrade, Jayson likes to ask, “Are the current relationships in your life related to your past or related to your future growth?”

If it’s mostly the former, it might be time to make a change.

Through school and college, society pushes us to grow until we’re 25. Then it becomes your job to keep growing. And if you don’t, you begin to die.

As Ben Franklin said, “Most people die at 25 and don’t get buried until 75.”

Recognize that Time & Energy are Scarce

Human experience is constrained by time and energy. This means all relationships, no matter how good, have opportunity costs.

The key to enriching your life is surrounding yourself with people who are batteries, not black holes. You want to be around people who energize you, not those who leave you drained.

The best way to do this is prioritizing people by personhood, not by accomplishment.

For example, Jayson spends little time with people who are toxic, inauthentic, or transactional, no matter how successful they are. He then reinvests this time and energy in richer relationships, helping him live the fullest, most enjoyable life he can.

If you want your best life, you need to deliberately prioritize relationships. If you don’t, circumstances will dictate your relationships for you.

Who You’re Around is Who You Become

Peer groups do more than just shape personality, they also set expectations.

In fact, most people’s lives are a direct reflection of the expectations of their peer group. This is why most Marines are at their highest standard while in the Marines. It’s easier to do hard things when the people around you are also pushing their limits.

As Jim Rohm said, “You are the average of the five people you spend the most time with.”

Always remember that proximity is power: who you’re around is who you’ll become.

What If Your Expectations Are Higher Than Your Peer Group’s?

If your expectations or ambitions are higher than your peer group’s, you have three options:

1.    Lift Them

Start by sharing your ambition to be better and invite your peers to join you. Some friends will jump at the opportunity, using it to grow. Others will dislike the change, which leads to your second and third options.

2.    Love Them

If someone doesn’t reciprocate your desire for growth, but you want to maintain relationship, you can love them where they’re at.

This means surrounding yourself with people who encourage your growth while continuing to pour into this specific relationship. It can be an incredibly generous thing to do.

Love your peers, just be careful they don’t perpetually pull you down.

3.    Leave Them

If someone saps your energy because you’re changing, it may be appropriate to leave them.

This isn’t an easy decision, but it may be a necessary one. To paraphrase Esther Perel, “Our relationships do not belong to us; they are on loan with the option to renew.”

It’s okay to let a relationship go, just be thoughtful about how you do it.

As always, avoid burning bridges unless absolutely necessary.

Closing Thoughts

At the end of the day, you can’t change the people around you, but you can change the people you’re around. 

Remember that your peer group is who you become.

Be gracious but choose wisely.

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Are you ready to become a world-class relationship-builder? 

Let’s get started!

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