Be Ready to Fail: Interview with Entrepreneur Rick Jordan

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I recently went one on one with Rick Jordan. Rick is a cybersecurity guru and tech entrepreneur.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth?

Rick: My dad's death for sure. My father passed away when I was 16 years old, and everything changed. I had to quickly go into this mode of figuring things out in order to take care of my younger brother and sister. My mother was obviously not very emotionally present. I mean, come on, she just lost her husband. I could never blame her for that. But at that point, my siblings were 10 and 11 years old, and I had to step into the role of taking care of the family.

Another pivotal point in my life was when I was laid off from BestBuy– this experience catalyzed my entrepreneurial journey.

I even had a near-death experience.

Being able to pull from how I handled my dad's death helped to shape how I handled the other traumas in my life. Even losing a half a million dollars in a failed venture two years ago...same skill set.

These experiences were all traumatic in one way or another, and I really do feel that traumas are completely instrumental for growth

Throughout life, you can keep chipping away and growing inch by inch. But it’s these big moments in your life, the ones that seem to blow things up, that actually blow you up. Meaning, level you up multiple notches in a very short period of time.

Adam: In your experience, what are the key steps to growing and scaling your business?

Rick: Getting yourself out of needing to have your hands in everything.

Now, this doesn't mean visibility. Because every CEO should have visibility into everything that's going on, but executing everything? That's reserved for the people you hired that are way better at doing those things than yourself.

There's no way that one person, including you, as a leader can have all of the necessary skill sets in order to scale a business regardless of size, large or small. We are humans, we are meant to do things as teams.

Be the motivator, be the person that inspires. Be the person that sets the direction. Everybody else will run through walls for you.

Here's a little secret on that: when your team asks you “how?” it's perfectly okay to say, “I don't know.” Because most of the “how” you're going to figure out along the way.

Vulnerability in front of your team as a leader is also extremely important. Just not at the expense of confidence.

Adam: What is your best advice on building, leading and managing teams?

Rick: Time! It takes a while to put the right team together. As you bring people on board, there are some that will be great fits for where you’re at right now. But as a leader, you have to be okay with the fact that the same people that started with you, may not be the same people that will be in the middle or the end with you.

The tenure for somebody to be useful to yourself and to your team could be anywhere from 10 years all the way down to just 10 days. There's many reasons behind that, of course, but that's what you have to identify. Just understand that the people that are there with you right now, are there for you in this moment.

It's almost like teams have seasons. It's really cool when you get those that end up sticking with you forever. The majority won't, and that's okay too! Help them flourish where they're at right now and then watch them soar with somebody else. That's the best compliment you can ever get as a leader, building a team. You prepare them for the next stage of their journey.

Adam: What are the most important trends in technology that leaders should be aware of and understand? What should they understand about them?

Rick: Remote workforces were necessary and helpful throughout the pandemic. But now we’re starting to see the reverse trend happen, which is something that I personally agree with. When it comes to technology, yes, it is extremely helpful in keeping your team connected and as productive as possible. But the best tech you need is a round table and some chairs. A place where everybody can sit down, come back together, and collaboratively problem-solve. And I'm in the technology industry! That's the crazy thing. There is so much great technology out there that keeps people connected across the globe, but there’s still nothing that substitutes being in person to get things done.

Adam: What do you believe are the defining qualities of an effective leader?

Rick: For me, confidence. Regardless of whether you actually have the answer or not (because you're still human and you're never going to have the answer all the time) your team will always still look to you as if you're the one that's supposed to have the answer. Imagine that weight on your shoulder! You always have to have an answer, even if you don't have the answer. That's when you shift into, “It's okay, we're going to find out what the answer is.” Which is still an answer in and of itself, rather than just giving them the answer that they're expecting. That's when you pull from the strengths of your team.

Passion is another because there's a lot of CEOs that I've met that don't really even care about what they're doing. They don't necessarily even believe in it, it's not something that they put all of themselves into. I know I'm just a guy, but I'm an All In guy. I’m passionate about the work I do because I don’t spend my time on things that will fade away. I only do things that have longevity and that I feel can help humanity.

The last but certainly not least would be authenticity. Everybody can spot somebody fake. Your team will be able to tell by your words, by your actions, and by your body language, if you really are who you say you are.

Adam: How can leaders and aspiring leaders take their leadership skills to the next level?

Rick: It's not a static skill set. It's ever-changing. Continuously place yourself in situations where you have to grow your leadership skills. Ways to do this are books, podcasts (like my podcast, All In with Rick Jordan), seminars and most importantly, mentors.

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?

Rick: 

  • Be ready to fail - if everything goes right all the time, you are doing it wrong.

  • Solopreneurs have limits - There are plateaus in doing things by yourself. You’re going to reach a point when the only way to accomplish more is with other people. Hiring people to fill the gaps in your own shortcomings is more effective than trying to improve your weaknesses.

  • Cash Flow gives you options - Cash Flow is more important than the amount of cash you have. The more money flowing in your business, through your business and out of your business, gives you more breathing room to get things done. Cash is not king, cash flow is king.

Adam: What are your best tips on the topics of sales, marketing and branding?

Rick: 

  • Sales - Move as quickly as you can to make sales and growth your only priority. And if you don't have the skill set or you don't want to do it, make it your priority to hire someone to do it for you.

  • Marketing - Understand your data. Don't just throw darts at a dart board. The only way you know if your marketing will really work is if you actually do it to test it out. Throw away all assumptions, raw data doesn't lie.

  • Branding - Your personal brand is the umbrella over everything that you do. Who you are is way more important than what you actually do. People will do business with authentic people.

Adam: What is the single best piece of advice you have ever received?

Rick: You are playing too small, don't minimize yourself or your dreams for any person including your own insecurities.

Adam: Is there anything else you would like to share?

Rick: Entrepreneurship can be a lonely journey. You will have people who do not believe in you, people who will hate on you, and never understand. None of that matters. In your darkest moments stay true to yourself and your vision. You will attract the right people to support you, walk beside you, and work for you. You will be ok.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

Follow Adam on Instagram and Twitter at @adammendler and listen and subscribe to Thirty Minute Mentors on your favorite podcasting app.

Adam Mendler