Rick Jordan, CEO & Founder of ReachOut Technology, speaker and author, and national authority on cybersecurity, business, and ethics.

How You Handle Hardship Determines Success

Cheryl Snapp Conner
7 min readJun 16, 2021


Tips for Life’s Hardest Moments as an Entrepreneur

The events of 2020 are behind us. The “new normal” has brought entrepreneurs some blessings, efficiencies, and surprising economies. The upheaval has accelerated markets such as e-commerce, video conferencing, and touchless payments and deliveries to a new level (has anybody not noticed the Chick Fil A check-out line? Kale salads and quick service for a double win). But for most entrepreneurs I’m hearing from, there are many aspects of business that are anything but sweetness and light.

I spoke this week with my friend Rick Jordan, the owner behind ReachOut Technology. You may recognize him from his stints on television as a cybersecurity and leadership expert. With a heavy focus on cybersecurity, his IT company grew by 40 percent during the pandemic. But Jordan is the first to tell me, the real stories of entrepreneurship are the ones we don’t generally hear — the loneliness, the barriers, and the life tragedies that are seemingly invariable along the path to success.

Rick Jordan on set of the All In with Rick Jordan podcast

It’s the biggest hurdles that galvanize strength

As I write this column, I’m sitting in the bedroom of a new second home. Now that it’s more viable to work from anywhere, I’m going back and forth between Salt Lake City and Eagle, ID to spend more of my non-working time with my elderly mom. It’s a wonderful opportunity to create a vacation home as an investment to rent and share with others, as well.

I had originally planned to build something new, to have the exact specifications that I was looking for, because the hot real estate market made it very hard to find something with everything I was seeking. But after a five-month journey to secure the new home, the construction projects fell through — twice.

So we turned our sights to existing homes. We made and failed to win five bids before securing a contract for a home a little smaller than planned, but with enough flexibility to meet our new needs. This deal also almost fell through in the 11th hour, due to the bank’s inability to manage sudden market demand, rising prices, and the added complexities of providing financing to an entrepreneur.

“You know that something will always go wrong. But you learn to address it, and you learn that this is when the blessings will come,” remarked Jordan during our chat.

When talking about business success in the aftermath of COVID, Jordan notes the global pandemic was difficult to navigate for him and his growing family, but it paled in comparison to two tragedies in his life that were larger still. The first was losing his father as a 16-year-old teen. This was the experience that galvanized Jordan’s resolve to take own life by the horns. Jordan had been at church preparing for a musical performance when the call came from his aunt to let him know that his father was passing away. “Can you come?” she asked. “Would he even recognize me?” he responded.

“No,” she conceded.

“Then I’m staying here,” he replied, and in teenage style he remained to perform on his drums.

As an adult, he regrets very much that his focus was elsewhere during the final hours of his father’s life, but the tragedy compelled him to learn, think, and act as a self-sustaining and enterprising adult from that moment forward.

Tragedy breeds accountability. Use it well.

This is not unique. Many entrepreneurs have similarly noted that the drive that propels them to work beyond comprehension is not the desire or tolerance for grueling labor. For many, it is born out of the fear of homelessness, poverty, or the inability to provide sustenance and safety for their children and families. For others, such as Jordan, the drive is a burning desire to create and control that stems from the fear that whatever the entrepreneur begins will fail without their personal touch.

In 2008, with newborn twins, Jordan had been laid off from his job. Entrepreneurship was not a choice, but an absolute necessity. Just several years later in 2015, Jordan’s second great tragedy was a deathly illness. His gallbladder failed and, as it was failing, “it sucked the strength from the other organs inside me,” he said. His failing health was now threatening to take the security he’d created away.

Jordan survived — lost 80 pounds — and developed a new respect for his physical health. But in the process, he learned (or perhaps relearned) that risk and fear are permanent parts of the entrepreneurial process. But having an outward facing purpose and a “why” for your efforts is the factor that will help you prevail.

“If it all went away, would I still be okay?” — Rick Jordan

Outward vs inward focus is key

The greatest entrepreneurs are outward focused, Jordan says — committed to moving the needle on an industry sector, to making a difference for a particular market, and to create wealth and opportunity for the company’s key players. Outward focus is rarer than you might think, Jordan says, but makes a critical difference in a company’s ability to forge the strength to move mountains.

For Jordan, it’s the need and the importance of “taking care of family” — the external company “family” that comprises your team — that gives you the resilience and purpose as an entrepreneur to carry forward in the face of every defeat.

Is it okay to have an inward focus? Yes, according to Jordan, but is more akin to a lifestyle job and a lifestyle business. These are valuable, too, but can only grow to a certain level. “I don’t see that as a true entrepreneur,” he says. “I see that as an owner operator.”

Where hobbyists and employees may hope or lobby for things to happen, a successful entrepreneur makes it so, as embodied by the famous accountability quote: “If it is to be, it’s up to me.”

Wealth may come and go, but purpose prevails.

Whatever the motivation, the experience of working incredibly hard leads to discipline and focus. For Jordan, one of the biggest keys, however, has been to learn over time to let go of the control when needed in order to allow your organization to grow.

“As an entrepreneur, the cycles of ups and downs are incredible,” Jordan muses in our visit. “You never forget the feeling of ‘brokeness’ and the fear that it could happen again. It’s the feeling of running a multimillion-dollar organization and knowing you’ve got less than $5,000 in the operating account.”

Jordan talks about a prior project in which he lost a half a million dollars in an event. The debt is now recovered, he notes. But it was in the heat of that failure that he became acquainted with Kevin Harrington, the original “Shark” from the ABC’s “Shark Tank.” It was out of failure that this hugely beneficial relationship began.

“Even if I imagine facing a massive potential failure, I know I would still be involved with people,” he says. “I would have to be. It’s never going to be a solo gig. Most importantly, it wouldn’t have anything to do with your worth as a human being.”

In his own case, “yes, a failure would mean increased stress,” he says, “But if everything crashed and burned tomorrow, I could go out the next day and start something new.”

“At a certain point in your life I’m sure you got your house, your car and you’ve been contributing to Social Security, and you know that no matter what comes your family wouldn’t be in the food line,” Jordan says. “You know that if the worst happened and you couldn’t control it, you would still be happy, still be home, and it would be okay.”

If it all went away, would I still be okay?

Conversely, he admits to currently owning a $20,000 Bulgari watch. “Is this worth it? Should I do it?” he recalls asking a professional friend. “If this and everything you own were to go away, would you still be okay?” the friend replied. He thought about it and said “Yes. Yes, I would.” So the watch took on no more meaning than it ought to, he concluded, and so he bought it and has enjoyed it, stress free.

“If it all went away, there would certainly be a ‘suck’ factor,” Jordan continues. “But personally, as an individual and as an owner of a company, I put the elements and functions in place to know that if the company went entirely away I would still be okay.”

In my own case, just before we went to settlement on my house, we had to pivot at the last-minute to a purchase in cash and near-term credit within the space of 24 hours. Even at this moment, we are not entirely out of the woods. I am confident I will prevail, but by the same token I have not slept for a period of 48 hours. However, it’s the greatest challenges that strengthens us and forge us into better entrepreneurs, along with comfort in the knowledge that if it all went away tomorrow, everything would still be okay.



Cheryl Snapp Conner

Cheryl Snapp Conner is founder and CEO of SnappConner PR and creator of Content University™. She is a popular speaker, author and columnist.