From Cold Outreach to Lifelong Friendships: How I Connected with Billionaires
Hey there, it’s Gordon! Ever wondered what it’s like to go from admiring business giants like Mark Cuban to calling them friends? I used to think these folks were out of reach, but through persistence, authenticity, and a bit of strategy, I built genuine relationships with Joe Polish, Adam Weitsman, and Jesse Itzler. In this post, I’ll share my journey of connecting with these incredible entrepreneurs and give you actionable steps to reach out to your own dream contacts. Let’s dive into how I turned cold emails into coffee chats and collaborations!
Why Reaching Out Matters
In today’s world, connections can unlock mentorship, partnerships, or life-changing advice. These aren’t distant celebrities—they’re busy people who value authenticity and mutual benefit. Mark Cuban, the Shark Tank star and Dallas Mavericks owner, is known for being approachable if you respect his time. Joe Polish, the mastermind behind Genius Network, thrives on building meaningful relationships. Adam Weitsman, the scrap metal tycoon turned philanthropist, loves ideas that align with his passions. And Jesse Itzler, the high-energy co-founder of Marquis Jet, connects through shared adventures and big dreams.
My story started when I was grinding on my 8-Day Wellness Challenge, a program to spark personal growth. I needed guidance to scale, so I took a leap and reached out to these icons. Here’s how it happened—and how you can do it too.
Mark Cuban: The Power of a Short, Sharp Pitch
Mark Cuban is a busy guy, but he’s open to direct, no-nonsense outreach. I’d read that he responds to concise messages that respect his time. Inspired by a story of someone landing a $1 million investment with a short email, I crafted a subject line that stood out: “How Your Shark Tank Bootstrapping Tip Shaped My Wellness Program.” The email was simple: one sentence about me, a nod to a specific Shark Tank episode where he talked about scaling lean, a brief pitch about my 8-Day Challenge, and a clear ask for 5 minutes of advice. No fluff, no attachments. To my shock, Mark replied in under 10 minutes, saying, “Sounds cool. Keep going.” I simply googled his email and have gotten a handful of responses over the years, from sending him an image when he was in Billions, to inspiration from his NFT ventures. We briefly met in the Miami Four Season’s lobby. Key takeaway: Keep it short, tie it to their work, and always follow through.
Joe Polish: Leading with Value
Joe Polish is the king of connection, running Genius Network, a hub for top entrepreneurs. I was 25 when I first met Joe at a National Speaker’s Association event with Brian Tracy. When everyone was asking about Richard Branson I asked about recovery and we quickly forged a relationship about that. We have since gone to many yoga classes. I have been to his house multiple times and met lots of friends and mentors through him. He has been one of the most influential people in my business journey. Introducing me to a man I can credit with over 500,000 in revenue directly too.
Lesson: Give before you ask, and focus on their mission.
Adam Weitsman: Aligning with Passion
Adam Weitsman turned a scrap metal empire into a platform for philanthropy and influence, with a massive Instagram following (@adamweitsman). I noticed his posts about giving back and saw a chance to connect over a bored ape. When he invited me to his penthouse, I jumped at the opportunity and went out of my way even though it was only supposed to be a 5 minute interaction. We text regularly and I always cherish out facetimes. He has helped me remember it is okay to work hard and struggle with mental health.
Tip: Start with a casual social media touchpoint, then formalize with a detailed pitch that aligns with their passions.
Jesse Itzler: Bonding Over Adventure
Jesse Itzler is a force—ultramarathons, living with Navy SEALs, and co-founding Marquis Jet. His energy is infectious, and his website’s contact form and active Instagram (@jesseitzler) make him reachable. After reading his book Living with a SEAL, I saw parallels with my challenge’s focus on resilience.
So I did what Jesse always does and cold called him. It let to me being one of his early members of his Build Your Life Resume community. I have gone with him to speeches and had the opportunity to go on many walks with him and his kids. I also just randomly showed up at his epic event Runningman which let to me dating one of the participants for 6 months. Jesse has a way of living that I wanted to learn from and I went all in.
Secret sauce: Connect on personal passions (like adventure) to build a real relationship.
Your Playbook for Reaching Influencers
My journey to befriending Mark, Joe, Adam, and Jesse wasn’t about luck—it was about strategy and persistence. Here’s how you can connect with your own dream contacts:
Do Your Homework: Study their work, values, and preferred contact methods (website forms, social media, etc.). Tailor your message to their world.
Craft a Killer Message: Use a specific, engaging subject line. Keep the body short: introduce yourself, tie your outreach to their work, and make a clear, low-pressure ask.
Lead with Value: Offer an idea, insight, or collaboration that benefits them. Show you’re not just taking.
Follow Up Smartly: No response? Wait a week, then send a polite nudge with new value (e.g., an update or fresh idea).
Build the Relationship: Once you connect, show up consistently—attend their events, act on their advice, and share your progress.
Use Tools Wisely: Platforms like Instagram, LinkedIn and Grok can help find contact info, but verify it’s legit.
Expect some non-responses—it took me dozens of tries to get these right. But every outreach is a step closer to a breakthrough.
The Ripple Effect: Why These Connections Matter
Befriending Mark, Joe, Adam, and Jesse didn’t just grow my network—it transformed my life Their advice helped me scale, their endorsements boosted credibility, and their friendships inspired me to dream bigger. These relationships are proof that bold, authentic outreach can change your trajectory.
So, who’s on your list? Take 10 minutes today to send that first message. It could be the start of something incredible. And if you’re ready to kickstart your own growth, join my 8-Day Wellness Challenge—it’s the same program that caught these titans’ attention.
Who are you reaching out to this week? Share in the comments, and let’s cheer each other on!
Connect... Gordon GordonBufton@Proton.me @GordonBufton