Oh Ship! Show Presents: Overcoming Obstacles as a Young Leader with John Hall

Success begins with investing highly in your personal brand at any age.

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John Hall, chief strategist of Relevance.com as well as co-founder of Calendar.com and Influence & Co., has been starting companies since he was in high school. In third grade, he started a “lunch brokerage” by selling the candy in his peers’ lunches to other grades at a markup. At 19, he and a friend bought and flipped their first house. “When I met friends in college, I would end up renting to them as a landlord,” he says.

That’s not to say his journey was easy. Read on for the key lessons John learned in overcoming the challenges faced as a young entrepreneur.

Building a Personal Brand

When John started out, he faced the typical obstacles of a young business leader. Namely, he had trouble being taken seriously due to trust issues. “Back when we were getting started, it was a huge barrier,” he says. “There are massive barriers that you deal with as a young entrepreneur, but if you’re able to overcome them by building and investing in your own brand and doing things, then it becomes a big strength.” The same goes for overcoming biases related to race and gender—investing highly in your personal brand can help you surmount obstacles.

Become known as a rising star

You can reframe youth as an advantage, John emphasizes. The Relevance team loves working with young leaders to help them get noticed in a big way. “Once you get them the right press placement, the right things going on with them, then everybody looks at it as a huge impressive thing,” he says. “They think, ‘Wow, that’s somebody who is a rising star.’ You want to deal with them. With Relevance, we love that kind of opportunity,” John says.

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Make sure you’re top of mind:

Here are John’s top tips on how to build your brand—and your business’s brand—as a rising star:


  1. Help others reach their goals. John’s book Top of Mind centers on how to support others in achieving their goals. “If you can help people with their motivations, then they’re going to help you in the future,” he says. His super-strength is helping people around him to consistently enhance their lives.
  2. Engage people in interesting ways. “If you read the book Top of Mind, the whole idea is engaging people in different ways with content, with action, with human connections, so that you’re on their mind at the right time and the right moments,” he says.
    Develop a great content strategy so people see your name consistently. “If you commit to that vision of owning an industry, you’re going to start showing up all over the place,” he says. “And content is one of the best ways to scale that.” A client with Hawk Media who wanted to own his industry now shows up in multiple top search results, not only for his own website but in a Forbes article.
  3. Choose a domain name wisely. Singular-word domain names that express something central to your product or service work best (like Calendar.com). This digital strategy will make your online presence more memorable and build credibility.

Taking these steps has a compounding effect over time, John notes. Like a magnet, these actions will continue drawing people to you.

Leading Across Differences

From early on, John has always worked to bridge differences as a leader. “If I hire all people like me, we’re gonna fail,” he says. Thus, his leaders cover a broad spectrum: they’re conservative, liberal, religious, and non-religious. 

How does John ensure strong teamwork despite these differences? 

  1. Leading by example. He embodies openness and respect for people of all walks of life. While he has certain strengths, like the ability to break through barriers, he needs people with other distinct skill sets to create a thriving team.
  2. Choosing the right people. “Focus on surrounding yourself with amazing team members, because your team is really what drives leadership,” John asserts. If others are invested in being good teammates, they’ll be able to look beyond their differences or find value in them.
  3. Admitting when he’s wrong—and avoiding idea bias. “I didn’t want to do that as a young leader; I thought that it showed weakness to admit when you’re wrong,” he says. If he could go back, he would get rid of his ego at a young age. This would also help him avoid being biased toward his own ideas. 
  4. Not permitting gossip and mistrust to spread. If someone complains to him about another person, he’ll ask if they’ve talked to that person first. He advises people to truly hear one another out.
  5. Being thoughtful to others. For example, when an intern was struggling, he gave her a $100 gift card and asked her to spend the afternoon with friends and come back recharged. This helped promote a culture of kindness.

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His Most Challenging Business Venture

John has experienced the challenge of quickly scaling up a service company as it rapidly expanded to different offices. But the technical challenges he experienced with Calendar.com stand out most. Since he’s not a coder or developer, producing new features proved challenging from a design perspective. “It’s very hard to tell people what to do when you don’t speak their language,” he remarks.

“Understanding conversions in a tech company compared to a service company was difficult for me,” he adds. Now, they’re seeing a high conversion rate, but they spent three years building up the product to reach that point.

Embrace the possibility of failure when starting a new venture, John advises. “Do your best, educate yourself the most you can, work hard to accomplish these things. If you fail, that’s okay,” he says. “Some of the best entrepreneurs fail four or five times before they have their big win.” Landing on an idea that aligns your competitive advantage and passion with opportunities in the industry will vastly increase your chances of success, he adds.

Surrounding Yourself with the Right People

Having the right people around you plays a guiding role in success, John affirms. Here are two important ways of doing that.

Choosing the right partners

Find someone who aligns with your values but has complementary skills to “create a super-power together,” John advises. While he tends to be a visionary, he’s had a long-term business partner who excels at operations and is incredibly resourceful.

“It’s also a journey. Going through it with someone is more meaningful than when you’re doing it on your own a lot of times,”  John reflects. It allows you to share both the failures and successes. Plus, it makes work more enjoyable through the daily banter and exchange of ideas.

Finding mentors everywhere

John doesn’t believe in having just one mentor. “What I’ve realized is that I want to surround myself with people that are all my mentors,” he says. “So my business partner is a mentor, my wife’s a mentor to me—my kids, I can learn a ton from my kids,” he says. Focus on building your network of mentors from a young age, giving you access to the level of collective wisdom that many people don’t find until later in life. 

By surrounding himself with the right people and building his brand, John overcame barriers that he faced in his younger days. Despite the challenges faced as a young entrepreneur, he steadily built an incredible reputation for himself, establishing himself as a key player in his industry!

Watch the entire episode of the Oh Ship! Show featuring John Hall and his personal brand.


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“Oh Ship!” is about celebrating the failures, sharing those stories, learning, and laughing along the way.

Freddie Laker

A veteran digital marketer with experience working with some of the world's biggest global brands. He now focuses on providing interim leadership to PE-backed firms.

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