Success Advice
How A 19 Year Old Kid Got The Chance To Work For Gary Vaynerchuk

“Crazy things happen when you know who you are. Certainty breeds influence”
This is the story of a new buddy of mine named Swish. I met him over Skype when my friend Joel Brown told me that we should chat. Within minutes of having a phone call with young Swish, I saw something quite incredible.
I couldn’t quite put my finger on it, but I knew that this chance encounter was going to change the way I think. As I got to know Swish through the few Skype calls I had with him, I learned something about him that blew my mind:
Swish had been headhunted to join Gary Vaynerchuk’s team in New York.
This is no small achievement. Gary is one hell of a successful man, and there are not too many people that haven’t read one of his books or listen to The Ask Gary Vee Show. His book “Jab Jab Jab Right Hook” changed the way I thought about asking my followers to do stuff.
So how did a 19-year-old kid get the chance of a lifetime? Read below.
1. Age means jack sh*t
Use your weaknesses to your advantage. Being nineteen could be perceived as a weakness. You have little life experience and are still finding your place in the world. Swish didn’t care about his age. He let his passion and enthusiasm light up the world.
The kid has infectious charisma and his certainty breed’s influence. He may not have all the answers at age nineteen, but he certainly doesn’t let you think that. Swish has started more businesses at nineteen than most people start in a lifetime.
He has a wearable tech company that is looking to change the game within the sports industry. Most people thought he was crazy and despite that Swish didn’t listen to them.
2. Surround yourself with winners
Swish didn’t have the contacts to get his wearable tech company into the NBA initially. What did he do? Hired Trevor Booker from the Brooklyn Nets NBA team to join his advisory board. You don’t need all the contacts; you just need to bring the right people with you on the journey.
3. Hustle harder than anyone else
Swish spends lots of time on social media. In the early days, Swish built connections with a few key people on Gary Vaynerchuk’s team via social media. He regularly tagged them in relevant posts. He shared his content with them.
What Swish did that very few do is hustle harder than anyone else. He’s a nice guy at his core so when he asks you to do something you feel compelled to hear him out. Swish is too cool and too nice to ignore. People are drawn to the guy because of who he has become.
He’s the kind of guy that everyone wants as their brother. I’ve often wondered what makes the difference between success and failure. People like Swish have shown me time and time again that it’s a strong work ethic, combined with an infectious human character.
Beautiful people on the inside are not the type of people to be lost in a crowd. Their spirit shines through and that’s what makes them get the results we all want. Swish getting the chance of a lifetime is no accident. It’s not chance. It’s not good fortune. It’s hustle.
4. Back yourself when no one else will
If you go back two years, most people hadn’t heard of Swish. He was unknown and finding his way in a sea of social media influencers. This didn’t stop Swish from following his dream. Fundamentally, like me, Swish is an entrepreneur.
He wants to make the world a better place through his various business pursuits, speeches and content. He’s cast a pretty wide vision and he achieves goals every single day that gets him towards his ideal life. People are drawn to that vision.
A vision for change and a vision for the future is what we all want. The trouble is there aren’t too many people that are bold enough to dream up a vision like this and then execute on it. I believe Swish is one of those people who will achieve the impossible.
There’s no way someone with that much guts can’t influence the right people to bring on the journey. Swish can’t achieve his goals alone and he knows that.
He’s taken the first step though which is backing himself above all else. He believes in himself and so it’s only natural that we will all start to believe too.
5. You have no freaking idea how powerful social media is
I think sometimes we forget the age we are living in. With enough patience, we can literally get in contact and build a relationship with anyone we want. A friend of mine said to me that this idea is limited. He said to me, for example, that if I want to get in touch with Tony Robbins via social media, I couldn’t.
That’s BS though. It would be challenging, but very achievable to get in touch with Tony via social media. High achievers won’t ignore you forever. If I sent messages to Tony and his team every single day and helped spread Tony’s message, then there is no way he would ignore me forever.
I’d probably have to follow this strategy for at least a year and that would require a high level of determination. My point is that I’ve seen it work before. It’s possible.
Swish followed a similar strategy to build a few key contacts that have transformed his life and career. Some of those contacts were part of Gary Vaynerchuk’s team. Next time you think that social media is some tool that everyone uses now and you can’t make a difference, think again.
Yes, it’s harder to cut through now on social media although I still think it’s way more powerful than many of us believe it is.
6. Mega successful people can see your greatness
Successful people have had to fight hard to get where they are. When they see other people, who are doing similar things to what they did on their way to the top they, sit up and take notice. Successful people can spot the same traits that they once relied on to build their careers.
In Swish’s case, Gary Vee saw the same hustle and storytelling ability that he had on his rise to fame.
“We all love an underdog who is just like us: the secrets sauce is that this underdog is happy to work his face off when others would have given up”
Persuade, inspire and influence people with your message. Tell your story even when you think no one is listening. There’s always someone listening and your brilliance will be discovered when the time is right. You must see your own brilliance first though.
If you want to increase your productivity and learn some more valuable life hacks, then join my private mailing list on timdenning.net
Success Advice
Why One-Size-Fits-All Leadership Will Always Fail (and What Works Instead)
The surprising truth about leadership styles that can make or break your team’s success.

Leadership has always been as much about people as it is about performance. Ken Blanchard, in his influential book, “The One Minute Manager”, put it simply: different strokes for different folks. (more…)
Success Advice
What Every New CEO Must Do in Their First 100 Days (or Risk Failure)
Your first 100 days as CEO could define your entire legacy, here’s how to make every move count

When Tim Cook took over from Steve Jobs at Apple, the world watched with bated breath. Jobs wasn’t just a CEO; he was a visionary, an icon, and a legend of innovative leadership. (more…)
Entrepreneurs
The Leadership Shift Every Company Needs in 2025
Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.

In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”
While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.
Why This Gap Exists
Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.
What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.
Tools and Techniques to Bridge the Gap
Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.
1. Practice Mutual Empathy
Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.
2. Maintain Professional Boundaries
Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.
3. Follow the Golden Rule
Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.
4. Avoid Micromanagement
Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.
5. Empower Employees to Grow
Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.
6. Communicate in All Directions
Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.
7. Overcome Insecurities
Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.
8. Invest in Coaching and Mentorship
True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.
9. Eliminate Favoritism
Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.
10. Recognize Efforts Promptly
Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.
11. Conduct Thoughtful Exit Interviews
When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.
12. Provide Leadership Development
Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.
13. Adopt Soft Leadership Principles
Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.
The Bigger Picture: HR’s Role
Mercer’s global research highlights five key priorities for organizations:
-
Build diverse talent pipelines
-
Embrace flexible work models
-
Design compelling career paths
-
Simplify HR processes
-
Redefine the value HR brings
The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.
Treat Employees Like Associates, Not Just Staff
When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.
Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.
Entrepreneurs
What Makes an Entrepreneurial Leader? Traits of the World’s Best Innovators
Inside the mindset of entrepreneurial leaders who transform risk, passion, and vision into world-changing results.

When you think of Richard Branson (Virgin Group), Bill Gates (Microsoft), Steve Jobs (Apple), Rupert Murdoch (News Corporation), and Ted Turner (CNN), one thing becomes clear: they are not just entrepreneurs, they are entrepreneurial leaders. (more…)
-
Change Your Mindset4 weeks ago
Why Ideas Are More Valuable Than Resources for Entrepreneurial Success
-
Entrepreneurs3 weeks ago
Building a Business Empire: Lessons from the World’s Boldest Entrepreneurs
-
Health & Fitness3 weeks ago
The Surprising Link Between Exercise and Higher Income
-
Entrepreneurs2 weeks ago
What Makes an Entrepreneurial Leader? Traits of the World’s Best Innovators
-
Entrepreneurs2 weeks ago
The Leadership Shift Every Company Needs in 2025
-
Change Your Mindset1 week ago
7 Goal-Setting Mistakes That Are Secretly Sabotaging Your Success
-
Success Advice6 days ago
What Every New CEO Must Do in Their First 100 Days (or Risk Failure)
-
Success Advice2 days ago
Why One-Size-Fits-All Leadership Will Always Fail (and What Works Instead)
1 Comment