👋 Hi all, Chris here! Today we’re talking about a few aspects of effective communication. I’ve been fortunate to host some of the world’s best communicators on the podcast and have had my fair share of experience as a former founder and venture capitalist. It's not just the words, but the energy, preparation, and presence to build the rapport to sell yourself and ideas.

So, I’m excited to get into it. And don’t forget to check out the latest deals at the bottom of the email. Also, please keep sharing stories of your amazing deals and if you find this email valuable, please consider sharing with a friend or colleague. Thanks!

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🤐 Overpitching is cringy, so say less

You know that feeling when someone is overselling or wraps up a long monologue with a clever closing line. Your politeness keeps you there, but inside you want to run. Overpitching, oversharing, or giving too much information… just doesn't work. People are repelled by the things that chase them. When you say less, you display more confidence and conviction and invite people to ask for more.

I spoke with award-winning Hollywood producer Brant Pinvidic (#67) about his "3-minute rule" to say less and get more. He believes every business, product, or service should be conveyed clearly, concisely, and accurately in 3-minutes or less. Don’t give all the details upfront; instead, give the other person a clear understanding that makes them curious and encourages them to lean into the conversation. The pitch is simply the door that leads to the discussion; it's the engagement that invites your audience to foster your idea.

✉️ Invite ownership to your idea

It's natural to treat your audience as buyers, especially when the conversation intends to persuade them (e.g., buy your product, invest in your idea). But that way of thinking is not optimal. Viewing your audience as builders who can grow your idea is much more effective. When you do this, you create a sense of ownership. People place a higher value on the things they put their effort into (IKEA effect) or already own (endowment effect).

Also, most decisions today are made by committee. You share what you heard with your boss or share an idea with a friend, and you do so in the way you heard it and felt it. That means the people who didn't hear the idea directly can influence the outcome. So you want your audience to feel a sense of ownership and value, so they can become a megaphone for your ideas. Inviting them in is only half of the equation because they also need to share your idea in the way you want them to. So don’t just give numbers, features, and perspective… you must tell a story. That's how they will remember.

🏰 Storytelling is not “once upon a time”

Storytelling has been a buzzword for a while, but it still has this reputation as 'once upon a time' (clearly, someone a long time ago marketed that well). Storytelling provides a natural flow of communication to lead the listener to a conclusion in an engaging and clear progression.

In my conversation with Suneel Gupta (#37), he discusses the importance of marrying a story with substance. We naturally desire to persuade with substance (think numbers, content, etc.). While the substance may keep up there, it’s the story that brings us in. One way to do this is to focus on a central character. Develop the story around that character to first build that level of understanding. Then, once you have done that, use the understanding and story of the character to zoom out and apply to the larger audience.

For example, when I was running my last company, which offered online financial planning, I always told a story of a couple that were friends of mine. They had recently gotten married and were struggling to figure out if they were on track for the financial goals they were planning together (house, kids, etc.). I shared what it was like for them to meet with an in-person financial advisor who asked them to print out bank statements and bring them to a sterile office. I used their journey to paint a picture of the problems we wanted to solve and it worked so well. Unfortunately, the company didn’t work nearly as well as the pitch, but that’s a story for another newsletter…

🪜 Structuring your message

There is an improvisational, off-the-cuff style that every communicator aims to master. It comes from two things:

A lot of practice (I'll get to this next)
Structuring and setting yourself up for the conversation

Planned conversations typically require sending materials in advance, which means the content for in-writing and in-person are going to take different forms. If you want the audience to read the slide, then put the words on there that you want them to read. If you are speaking out loud and want them to listen to you, don't put the words on the screen that will reshift their attention. Use images or bullets that will enhance whatever you are saying. Your slides should support you, not do the work for you.

When I build presentations, I try to put almost nothing on my slides – usually just an image or 1-3 words. I also want to know the content so well that I can move through the conversation more seamlessly. It allows me to drive home the point I want to make, but in a way that might evolve after reading the room. If there are words on the slides, I have locked myself into how I deliver the message.

Finally, I can't talk about structure without mentioning Brant's WHAC method. It's a simple organizational formula for giving a great pitch.

W - What is it? Inform your audience of what you are offering.
H - How does it work? Explain simply and clearly how your idea works.
A - Are you sure? Give them validation for your claims.
C - Can you do it? Prove that you can put this into action.

I’ve tried to put this method to work when I pitch All the Hacks (feedback welcome):

All the Hacks is a top ranked podcast with a goal to help listeners upgrade their life, money and travel. The show just hit 1m unique listeners since launching last year and I’ve hosted a number of incredible guests like Tim Ferriss, Dan Pink and Kerri Walsh Jennings.
As for me, I’m an entrepreneur and life optimizer who’s founded/sold two companies, racked up 10+ million points and miles, traveled to 60 countries (mostly for free in first class) and am on a quest to help everyone live happier, healthier and wealthier lives.

🎯 Putting in the practice

My biggest piece of advice for when you are presenting, pitching, or selling is to avoid reading your notes. It gets awkward, and if your audience is too consumed with that feeling, they don't listen to your content.

Practice enough that you don't need to speak with notes.
Get comfortable knowing that you will forget things, and that it’s ok. If it’s important enough, it will resurface later.

Suneel’s research found that the best communicators, on average, practice 21 times before delivering the real deal. And we aren't talking about the 'director's commentary' either. You must go through the presentation as close to the natural environment. Use the words and slides you plan to use. Pitch your spouse, kids, friends or colleagues. You can even go as far as practicing at the same time of day that you are planning to give the presentation. It's about building the right muscle memory.

😵 Steer into the objection and own the negative

I love calling out objections upfront. I used to say, "Look, I don't have XYZ information yet; if that means you aren't even interested to hear me talk, we can end this meeting early and save you time." Not only does it add credibility, but it also doesn't become a distraction in your audience's mind during the entire pitch. You've owned it. Also, by having an objection, you invite the audience to share their solutions to the problems or ideas, giving them ownership. Everyone likes to be a hero to a problem. Let them be.

There are still some objections that you can’t overcome. If you provided the information clearly enough for them to understand it, but they still aren't engaging, move on. It takes so much effort to turn a 'no' into a 'yes.' Other people are interested and believe in it, so don't waste your time trying to change a ‘no.’

To make this easy, I like to give people a simple out. When I was raising money, I always followed up with:

“Really enjoyed our conversation! Things are moving along, so just wanted to see if there’s anything else you need from me to help with your internal discussions. If not interested, just let me know..”

I wanted to make it easy for someone to say 'no,' so we get to the answer faster and reduce the anxiety of not knowing what they will say. If they don't see the value, let it go and find someone else.

📣 Getting Feedback

I can't stress hard enough how valuable feedback really is, and there are three great ways to gather it:

The first is to build a circle of people around you that will offer you the feedback that will elevate your idea. In Suneel’s book Backable, he describes the four types of people you could include:

The collaborator is the person that helps you build on your idea with an eye on market fit and demand.
The cheerleader is the person that gives you the energy to propel you forward.
The coach is the person that tests your idea to make sure it fits you as a person.
The critic is the person that pokes holes in your idea.

While a single person can be more than one, what's most important is that you set expectations as to which type you need in a particular moment.

The second is reading between the lines. Pay attention to the questions people are asking you to get accurate answers. For example, if the people are asking questions that you're eventually getting to, it might indicate that your presentation is out of order. If the questions were trying to comprehend what you just said, it means you probably weren’t clear enough. The questions people ask you are indicators of how well things are going.

The third is direct feedback. It's taking critique, owning it, and applying it. I used to write down every question an investor asked in a pitch meeting. I would make a single slide of just that addressed the question for the next pitch and drop it in the appendix. So I had this short, sweet deck with dozens of appendix slides in case someone asked a question I had heard before. It had an added benefit instilling more confidence than if I had just said it on the fly. On the off chance you don’t get questions, you can always try asking:

What part of all that stood out the most?
How would you describe this idea to someone else?
What could I have done to make this a 9 or 10?

And then use the info you collect to improve for next time.

💯 Stand out by doing the things others don't

My final piece of advice is do the things that people typically won't do. Find the unique insight that doesn’t show up in Google or demonstrate a level of effort above the norm. Even if what you share doesn’t end up being valuable, the effort you demonstrate is often worth it. When I was hiring, it’s remarkable how most candidates all do the same thing, but the ones that don’t always stand out.

I once reached out to a company I wanted to work at and told them that I made a presentation about their industry that I wanted to share with them. Looking back, the presentation was terrible, it had no unique insight and probably added no value to the company. But the fact that I made the presentation showed them that I did care. Standing out made all the difference and I was working there a few months later.

💵 Latest Deals

Here are the top deals I’ve seen in the past two weeks:

💳 150,000 United Miles with the United Business Card

Chase just increased the signup bonus for the United Business Card from 75k to 150k United miles. It does require spending $20,000 in the first 6 months, but the $99 annual fee is waived for the first year. I value United points at ~1.2¢, so this bonus is worth ~$1800. Also if you’ve never applied for a business card before, check out this article, because even if you sell things online or do some freelance work you might be eligible. You can sign up here.

💸 10-20% Off with Chase Offers

I don’t usually see Chase offers worth adding to my cards, but right now I’m seeing some great ones to get 10-20% cash back at Home Depot, Best Buy, Chipotle and more.

🏨 Double Points at Hyatt

Hyatt’s latest promotion is offering double points and double elite nights on stays of 2+ nights between 9/15 and 12/20. You just need to register here before 11/15.

📺 Free Paramount+ with Amex Platinum

When Amex announced that Platinum cardholders would get free Walmart+ last year it wasn’t that exciting. However, Walmart just announced that starting next month, all Walmart+ members would get free access to Paramount+. You can see the shows and other content they have here.

🏨 IHG Award Flash Sale

IHG is currently having a sale allowing members to book rooms with points at some of their most expensive hotels for 50% off. I’m not sure how long this will last, but you can read more here.

🎙 Recent Episodes

#72: Increasing Productivity, Procrastinating Less and Living a Happier, Healthier Life

Entrepreneur, YouTuber, and former doctor, Ali Abdaal, discusses strategies, tools, and hacks to live a happier, healthier, and more productive life, including how to dial in productivity, ways to combat procrastination, strategies to read more efficiently, and his favorite apps to organize, process, and store information. Thank you to Vuori, Dry Farm Wines and Athletic Greens for sponsoring this episode!

🎧 Listen to Ep 72 w/ Ali Abdaal

#70: 52 Places: The Art of Traveling Like a Journalist and Making Every Trip Memorable

Expert traveler and journalist, Sebastian Modak shares his learnings from traveling to 80+ countries and living on four continents, including what it means to travel like a journalist, how he uses those skills to plan a memorable trip, some of the unusual experiences he's had on his journeys and why travel is important for everyone. Thank you to TrueBill, Inside Tracker, Wren and Daffy for sponsoring this episode!

🎧 Listen to Ep70 w/ Sebastian Modak

💭 Parting Thoughts

Thank you so much for reading! How’d you like this one? (click an emoji)

❤️ | 🙂 | 😐 | 🙁 | 😡

Your feedback will help make it great, so I’d love to hear your thoughts/suggestions. Please feel free to respond to this email and I promise to read and respond to every one. If there’s a topic you’d love me to dig into in an upcoming issue, please let me know.

Best,

Chris

Today, I’m grateful for the support of our partners Vuori, Dry Farm Wines, Athletic Greens, TrueBill, Inside Tracker, Wren and Daffy.

Chris Hutchins works at Wealthfront. All opinions expressed by Chris and his guests are solely their own opinions and do not reflect the opinion of Wealthfront. This newsletter is for informational purposes only and should not be relied upon for investment decisions.

All the Hacks

📣 Pitching & Effective Communication …