SOLO | Make Money By Having the Conversations You've Been Avoiding, part 2 episode artwork

EPISODE · May 18, 2026 · 19 MIN

SOLO | Make Money By Having the Conversations You've Been Avoiding, part 2

from Travis Makes Money · host Travis Chappell

On this solo episode, host Travis shares a personal, behind-the-scenes look at how strategically reaching out to people you admire can transform your career and expand your sense of what is possible. Drawing from his own experiences in podcasting and entrepreneurship, he walks through how he went from dreaming about conversations with icons like Shaquille O’Neal and Joe Gatto to building real relationships with them over time. On this episode we talk about: How a “dream guest” list turned into real conversations with Shaquille O’Neal and Joe Gatto Why proximity, rejection therapy, and exposure change your sense of what’s possible A 30-day outreach challenge to build relationships through cold DMs How to structure short interviews and reuse the same core questions for different guests What to say in a DM (and what to absolutely avoid, including AI-written outreach) Top 3 Takeaways Your sense of what’s possible expands as you consistently put yourself in proximity to people you once thought were unreachable, even if it starts with a simple DM. Focus on inputs you can control—like sending five personalized cold DMs per day for 30 days—instead of obsessing over outputs you can’t guarantee, such as who says yes. Lead with genuine value and specificity in your outreach: personalize your message, keep it short, make a clear ask, and reduce friction so busy people can easily say yes. Notable Quotes “Every real conversation removes a little bit of the intimidation tax that you’ve been paying your whole life leading up to this point.” “The point is not that every successful person becomes your mentor; the point is that your sense of what’s possible continues to expand.” “For the love of God, please do not have AI write your DMs for you—if you don’t know how to write a 50-word outreach, that’s exactly what you should be working on.” Connect with Travis:        Instagram: https://instagram.com/travischappell        Other: https://travischappell.com A Word from Our Sponsors: - Are you ready to start your own creatorjourney and make it big? Visitwww.fanvue.com today and launch yourcareer! - To learn more about Mode Mobile and its investor community, go tohttps://invest.modemobile.com/travismakesmoney-Travis Makes Money is made possible by High Level – the All-In-One Sales & Marketing Platform built for agencies, by an agency.Capture leads, nurture them, and close more deals—all from one powerful platform.Get an extended free trial at gohighlevel.com/travis Learn more about your ad choices. Visit megaphone.fm/adchoices

On this solo episode, host Travis shares a personal, behind-the-scenes look at how strategically reaching out to people you admire can transform your career and expand your sense of what is possible. Drawing from his own experiences in podcasting and entrepreneurship, he walks through how he went from dreaming about conversations with icons like Shaquille O’Neal and Joe Gatto to building real relationships with them over time. On this episode we talk about: How a “dream guest” list turned into real conversations with Shaquille O’Neal and Joe Gatto Why proximity, rejection therapy, and exposure change your sense of what’s possible A 30-day outreach challenge to build relationships through cold DMs How to structure short interviews and reuse the same core questions for different guests What to say in a DM (and what to absolutely avoid, including AI-written outreach) Top 3 Takeaways Your sense of what’s possible expands as you consistently put yourself in proximity to people you once thought were unreachable, even if it starts with a simple DM. Focus on inputs you can control—like sending five personalized cold DMs per day for 30 days—instead of obsessing over outputs you can’t guarantee, such as who says yes. Lead with genuine value and specificity in your outreach: personalize your message, keep it short, make a clear ask, and reduce friction so busy people can easily say yes. Notable Quotes “Every real conversation removes a little bit of the intimidation tax that you’ve been paying your whole life leading up to this point.” “The point is not that every successful person becomes your mentor; the point is that your sense of what’s possible continues to expand.” “For the love of God, please do not have AI write your DMs for you—if you don’t know how to write a 50-word outreach, that’s exactly what you should be working on.” Connect with Travis:        Instagram: https://instagram.com/travischappell        Other: https://travischappell.com A Word from Our Sponsors: - Are you ready to start your own creatorjourney and make it big? Visitwww.fanvue.com today and launch yourcareer! - To learn more about Mode Mobile and its investor community, go tohttps://invest.modemobile.com/travismakesmoney-Travis Makes Money is made possible by High Level – the All-In-One Sales & Marketing Platform built for agencies, by an agency.Capture leads, nurture them, and close more deals—all from one powerful platform.Get an extended free trial at gohighlevel.com/travis Learn more about your ad choices. Visit megaphone.fm/adchoices

NOW PLAYING

SOLO | Make Money By Having the Conversations You've Been Avoiding, part 2

0:00 19:00

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

いろはにマネーの「ながら学習」 IrohaniMoney この番組では、インターン生2人が、金融、経済、投資関連の気になる情報を分かりやすくお伝えしていきます。インターン生の会話を「ながら聴き」する感覚で一緒に勉強していきましょう!ご意見箱フォーム:https://forms.gle/TTGaVP2TJksNMKJo7ぜひお便りや感想をお待ちしています!公式X:https://x.com/irohanimoney番組のハッシュタグは「#いろはにながら」です。番組への感想をお待ちしています!いろはにマネー:https://www.bridge-salon.jp/money/姉妹サイト:https://kabu.bridge-salon.jp/姉妹サイト:https://bridge-salon.jp/(株)インベストメントブリッジ運営 Rich Dad's Guide to Investing II Robert T. Kiyosaki II Full Audiobook II Robert T. Kiyosaki Investing means different things to different people… and there is a huge difference between passive investing and becoming an active, engaged investor. Rich Dad’s Guide to Investing, one of the three core titles in the Rich Dad Series, covers the basic rules of investing, how to reduce your investment risk, how to convert your earned income into passive income… plus Rich Dad’s 10 Investor Controls.The Rich Dad philosophy makes a key distinction between managing your money and growing it… and understanding key principles of investing is the first step toward creating and growing wealth. This book delivers guidance, not guarantees, to help anyone begin the process of becoming an active investor on the road to financial freedom. Mindfulness for gamers Shaun Donaghy / Pickaxe Unlock your gaming zen and discover the secret to improved mental health! Dive into mindfulness with guru Shaun Donaghy as he makes understanding meditation easy and fun. Learn to release anxiety and sadness and level up your joy. More than a podcast – it's your ticket to a happier gaming life! Mobile Money by moomoo Mobile Money by moomoo Hear from seasoned traders, financial influencers, and industry insiders as they discuss money matters and market news and share their personal finance stories.Disclaimers: https://www.moomoo.com/us/support/topic4_523

Frequently Asked Questions

How long is this episode of Travis Makes Money?

This episode is 19 minutes long.

When was this Travis Makes Money episode published?

This episode was published on May 18, 2026.

What is this episode about?

On this solo episode, host Travis shares a personal, behind-the-scenes look at how strategically reaching out to people you admire can transform your career and expand your sense of what is possible. Drawing from his own experiences in podcasting...

Can I download this Travis Makes Money episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.
URL copied to clipboard!