A $50,000 Investment in Growth: My Journey with VaynerMedia’s vYve Program


Last year, I made a bold decision (probably an understatement): I invested $50,000 in Vayner Media & The Sasha Group’s "vYve" program, a high-performance accelerator launched by Vayner in May of 2024. Spoiler alert—it was one of the best decisions I’ve ever made as an entrepreneur. Here’s why I did it, what I gained, and why I’d do it again in a heartbeat.


The Spark: A Deep Dive with Gary Vaynerchuk

My journey began in 2023 with Gary Vaynerchuk's "4D's" program—a one-day deep dive on digital business trends, capped with a 1.5-hour Q&A with Gary himself. Little did I know that I would meet a few people that day that would drastically change the trajectory of my entrepreneurial journey.

Quick Side Story: 4D's was to take place in New York at Vayner offices and I am in Florida. I brought one of my best friend's, Ike, with me to film the 4D's and some BTS. We were boarded on our plane in West Palm Beach when the pilot came over the intercom, "we will be postponing this flight for at least a few hours...". Ike and I didn't have time to wait and potentially miss the 4D's day. We started our drive from West Palm to New York immediately.

We made it to New York the next day with 1 hour to spare before the intro-dinner. Whew.

Ike somewhere in Virginia

What seemingly could have stressed a lot of people out (having to drive from FL to NY and then back) ended up being a super fun time for Ike and I to strengthen our friendship and share so many fun memories along the way.

Back To The Main Plot:

At 4D's, I connected with James Orsini , a brilliant mind at Vayner/Sasha Group, who later pitched me on vYve: “What if we could deliver the 4D experience, but on steroids?” I was all in.

Spearheaded by Andrea Sullivan (President of vYve and former CMO + CCO of Vayner Media), vYve promised a 120-day journey for 10 carefully selected entrepreneurs and executives. James + Andrea = 2025 Super Heroes (if you know, you know). James was the brain and connector and Andrea was the heart and soul. They each cared immensely for each one of the vYver's success in the program. Our cohort was diverse in skills and industries but united by one thing: curiosity. We had some serious entrepreneurs and executives in our group - this was another huge reason I wanted to join - to be able to learn from people actually doing it.

The Experience:

The first two days were a total surprise. Since were were the first ever cohort, there were a lot of fun surprise and delight moments along the way. This time in New York was even better than the last (during 4D's). I got to bring Ike again but also my wife, Tia, and her best friend ,Olivia, (who has worked with Get Up And Go Kayaking for 5 years) who all joined in the adventure. We got to spend time hanging out, exploring the city, and then getting into vYve! Timing was so cool, I had just received notice from Visit Orlando that they had featured my business on a billboard in Time Square. Tia and I got to see the billboard and it felt like a full circle moment of the 8+ years of hard work we had put into the business.

How freaking cool is that!

Day 1 we got to meet the others in the program and we were instantly put outside of our comfort zone (did I mention I hate heights).

Photo cred Brent Szklaruk-Salazar

We were shown around NYC and had an amazing time at the Top Of The Rock, followed by lunch, and then over to NASDAQ where we closed the bell with Gary and many others friends & family from the Vayner world. Gary had just released his new book - Day Trading Attention - and we got to witness a fireside chat directly after NASDAQ. Then we got back together for a dinner at Little Maven filled with even more brilliant minds and exciting conversations. These were the rooms I had always dreamt of being in. The people, the topics, the atmosphere, the feeling, all felt right.

Ike and I at NASDAQ

Day 2 we all got back together early in the morning and jumped right into the official programming. However, instead of diving straight into business strategies, we focused inward—sharing personal stories, summaries of our life story, stepping out of our comfort zones, and bonding over an amazing meal by Palak P. (Chef Palak) and Mona (which Gary popped in to join us for). I knew I’d found my kind of people. Maybe some of you entrepreneurs or execs will relate - sometimes this journey is lonely, sometimes it is overwhelming, sometimes it is demanding, it's hard to find a strong group of people that get it.

Over the next 120 days, we learned from an incredible lineup of speakers:

We also had the privilege of working with an executive coach, Dr. NaTasha , whose 1:1 sessions helped me create actionable plans for my business and personal life. I’d never had a coach like this before, but the impact was undeniable and invaluable.

A highlight was attending VeeCon, where I saw Gary’s work ethic up close. After a grueling day of 5+ hours of meet-and-greets, and running his conference, he drove 30 minutes to join us for an impromptu dinner during arguably one of the busiest weeks of his year (it was also 10PM on a night that he knew he had to be up the next morning to do it all over again). If you ever doubted Gary’s passion for his work, that moment would change your mind.

We also got to check out they Vayner Offices in LA which was pretty awesome. We got to sit in on a talk by JT Barnett, Michelle Gonzalez, Adrienne Lahens and Peter Chun about TikTok and how Creators & Brands can level-up creative. As well as a fun surprise session with Mike Boyd Jr + Trinidad James (a personal highlight)!

The Grand Finale: A Transformative Summit

The program concluded at the Modern Elder Academy (MEA) in Santa Fe, led by the founder Chip Conley, author of Learning to Love Midlife, Wisdom @ Work, and PEAK: How Great Companies Get Their Mojo from Maslow --- amongst others. Over 2.5 days, Chip’s insights on transformational moments and leadership left me with countless “aha” moments. The first day in Santa Fe we went on an 'awe walk' with Chip where I got to spend an extremely memorable 15 minutes walking alongside of Chip to discuss some travel-industry trends, share thoughts on business, and I got to share a little bit about Get Up And Go Kayaking.

Chip's ability to find the wisdom in life moments is truly unmatched. We spent a lot of time with Chip and learning from the great depths of ideas that he has to share.

This photo does an amazing job of capturing my admiration of Chip. Photo by Miles Diggs.

The staff, food, accommodations, and atmosphere at Modern Elder Academy are top notch. Sue Izzo is a GEM. She led sessions and facilitated the programming of our time at MEA and it was perfect.

One Last Side Story 🍊 (it's a good one, I promise):

Some of you have heard the story about my first ever tour guide, Alex, who unfortunately passed away while free diving on his day off. Alex had taken a risk on me and the business in its infancy. I spent a lot of time with Alex on the water and he taught me things about the waterways that I hadn't known myself. One standout moment was when he pointed out a wild orange tree that I hadn't ever seen myself (and I had taken 50+ trips up and down that exact river). He then went on to tell me all about wild oranges and how they taste compared to farm grown. The day after that I had learned that Alex had gone missing while free diving I had to cover his tours on the water. While we reached the prettiest part of the waterway (the top of Rock Springs Run for those of you familiar) there was a wild orange floating down the middle of the river and right alongside my kayak. I grabbed the orange, picked it up, and ate it. It was my sign from Alex (who hadn't yet been found) that he had passed but also that he was OK and at peace. We now dedicate the anniversary of his passing each year as a fully charitable day at my locations. Alex still sends me signs from time to time.

How does this tie into the vYve experience?

Well... one of the days at MEA there was a scheduled 6:45am hike up a ridge to enjoy the sunrise and dawn. Lee (who is an amazingly kind, caring, loving cowboy) from MEA led the hike and even took off his boots along the way which prompted a few of the ladies in vYve to do the same and feel more in tune with the land. We stopped at a small shack where they told us a story of "milagros", which in Spanish translates to "miracles". They took out a bag full of trinkets that we were to reach in (without looking) grab one and hammer to the side of this small wooden shack. I reached in, grabbed the first one I touched, and pulled it out of the bag. When I saw it, I knew, but I had to ask Julia and Habib what they thought it was. Sure enough, it was an orange. Out of the thousands of small trinkets, I got the orange - thank you Alex.

Here's what the trinkets looked like. Now you can see why it was amazing that I grabbed an orange out of all of the random options. Photo by Miles Diggs.

We then summited the ridge and enjoyed the dawn in silence. Fittingly, Andrea turned on a song on her phone that meant so much to her. The group of us all had our own deep moments while on the ridge. As I was reflecting on what just happened with the orange, my memories of Alex, my entire journey as an entrepreneur, it all felt very full circle and meant to be. I was where I was always intended to be.

Here's that ridge. Photo by Miles Diggs.

We ended this journey as we began—looking inward, reflecting on how to be the best version of ourselves, how to be empathetic leaders, how to foster a caring community, and how so much more. We even spent time with horses which was remarkable and I learned more than I had thought was possible. This was the perfect setting for these moments.

The Takeaways: More Than I Could Have Imagined

Throughout vYve, I laughed, cried, got vulnerable, cheered, danced, and learned more about myself than I thought possible. I was finally in rooms with people actually doing it—leaders who inspired me to elevate my game. The program delivered leadership and growth-mindset transformation alongside business and wellness insights.

I walked away with lifelong connections, actionable strategies, and a renewed sense of purpose.

A Shoutout to My Support System

I couldn’t have done this without my amazing wife, Tia. She held down the fort—managing our home and animals—while I was out learning and growing. She came with me to New York and to LA during the program. She pushed me to be present in every meeting and listen, learn, and take action. Her support allowed me to fully immerse myself in this experience, and I’m endlessly grateful.

Habib, Jia, Ronsley, Tia, and I at the VeeCon dinner

Would I Do It Again? Absolutely.

To Gary, Andrea, James, Dr. Natasha, the vYve 1.0 crew ( Ace Alfalla Habib Salo Jasmine Star Jeanelle Teves Kari Warberg Block Ronsley Vaz Jessica Saavedra Mandy Rassi Jia Hyun ), and everyone at Vayner + The Sasha Group and the Modern Elder Academy: thank you for the memories, breakthroughs, and lessons that will stay with me forever. vYve wasn’t just an accelerator—it was a life-changing journey. Thank you Julia Balick - you were a huge reason for the overall amazing experience and we shared so many good laughs, memories, some tears, and even some questionable dance moves (I'll spare everyone the details) - haha!

I need to write an article just on the other people in vYve 1.0 - each of you inspired me in ways that I didn't know were possible. Grateful for all of our conversations, Mighty Networks chats, Uber rides, bus rides, dinners, staring into each others eyes (haha), campfire singalongs, walks, wagon rides, horse chats, reframes, 1:1's, and so much more.

If you’re an entrepreneur or executive looking to supercharge your growth, I can’t recommend vYve enough. It’s a space to be vulnerable, get inspired, and do the work—together. Reach out if you want to learn more - glad to share. Trust me, you won’t regret it.

What’s been your most transformative professional experience? I’d love to hear about it in the comments! 👇

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Photo by Miles Diggs

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