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Waldo Waldman

Episode 18: The Professional Networking Tips and Mentorship Advice You Need to Be Successful, with Waldo Waldman

Lt. Col. Rob Waldman “Waldo” — was his call sign — he’s the author of the New York Times and Wall Street Journal bestseller “Never Fly Solo.” A graduate of the Air Force Academy, Waldo is a decorated combat fighter pilot and an expert in helping leaders and organizations accelerate performance in changing environments with his professional networking tips and mentorship. Waldo overcame massive claustrophobia and a fear of heights to become a fighter pilot and believes that the key to building a culture of trust lies with your wingmen the men and women in your life who help you to overcome obstacles, adapt to change, and achieve success. In business and life, you should never fly solo! Waldo is also the founder and President of The Wingman Foundation, a 501(c)(3) whose mission is to build funds and awareness for soldiers, veterans, and their families in need. Waldo is an inductee into the professional Speakers Hall of Fame and his clients include Marriott, Hewlett-Packard, UPS, and Verizon. He’s been featured on Fox & Friends, CNN, MSNBC, Inc. Magazine and The Harvard Business Review.

What you’ll learn about in this episode:

  • Waldo’s background
  • Why you need a mentor (and why finding a mentor was the first thing Waldo did when switching careers)
  • Waldo’s professional networking tips
  • How to find the time to get into an industry while employed at a different job
  • Why you need to hire an assistant sooner than you think
  • Why you need to be involved in mastermind groups of likeminded professionals that don’t necessarily share your profession
  • How to seek out mentors a couple levels above where you are
  • Why Waldo wrote his book “Never Fly Solo”
  • Why fearlessness is a myth and why you need to face your fears
  • Waldo’s next challenge: figuring out how to monetize his business outside of speaking engagements
  • Waldo’s next book

Ways to contact Waldo:


Welcome to System Execution, the strategy and system behind today’s successful companies. Systems can make or break your company, but here we’ll solve your physical, technological and psychological systems issues by connecting you with experts that have succeeded in overcoming those challenges in their own business and providing you the guidelines and tools you need to implement those same strategies for immediate results. Now here’s your host, Vera Fischer.

Vera: Welcome to System Execution, a podcast devoted to using processes and systems to drive to a better outcome for your business. I’m Vera Fischer, your host. All businesses no matter the size relies on systems. Some of these are physical systems such as a factory. Some are technological like project management software, while others are psychological systems such as checklists and organizational charts. Many of these systems will overlap in your business. Today’s guest, retired lieutenant colonel Rob Waldo Waldman, known as The Wingman, is a hall of fame leadership speaker and author of the New York Times and Wall Street Journal bestseller “Never Fly Solo.” Waldo is a highly experienced combat veteran with over 2,650 flight hours and 65 real world combat missions.

Having flown both in Iraq enforcing the No Fly Zone and in Yugoslavia during Operation Allied Force in 1999. Some of his military honors include five Air Medals, two Aerial Achievement Medals, four Air Force Commendation Medals and two Meritorious Service Medals. Welcome to System Execution, Waldo.

Waldo: Great to be here, Vera.

Vera: Well, we are really excited to have you. I know my listeners are waiting with bated breaths to hear what your professional networking tips and what you have to say about never flying solo. Before we get started, can we hear a little bit more about you and your experience and what brought you to writing this book?

Waldo: I so appreciate being on the show because I guess there’s no more relevant environment when it comes to execution in my opinion than in the military, in particular in an F-16, flying a sophisticated aircraft with a wingman, men and women, who you fly with who are depending on you for their lives. Execution is a very, very important factor in my life. I graduated with the Air Force Academy. I was an instructor pilot first in the Air Force teaching young men and women how to fly. Then I was an instructor instructor teaching people how to instruct which is really different than just instructing especially when it comes to processes and execution. Teaching is a process and you have to understand that and have a big passion and be very relevant to the people that you’re trying to teach.

Anyway, went into the F-16. Was blessed to fly the aircraft and was deployed to Iraq and Kosovo. 65 missions and I was shot at which kind of will change your life and make you even more reliant on execution and teamwork. Then when to graduate school. Became a high tech sales person and then was in mergers and acquisitions commission only sales for years before deciding to take the leap and start my business as a speaker sharing my philosophies about success, about relationships and commitment and courage. I got inducted in the speaker hall of fame and I’ve been doing this 15 years and I love what I do. I love helping people. That’s the summary.

Vera: Well, that’s really cool. I’m mesmerized I guess by the being shot at. I guess that would definitely change your life without a doubt.

Waldo: Yes. It makes you realize how important it is for you to prepare before you strap in and do a job. We planned our missions. We had contingencies. We knew our systems. We knew our technologies because God forbid if that missile was coming, you can’t wing it. Right?

Vera: Exactly.

Waldo: You got to prepare. It really reinforced the fact that we have to get up and not wing it and execute as well as possible because there was a lot at stake.

Vera: Waldo, when we were talking earlier, there were a couple of instances where you had mentioned really switching careers and really moving into a zone that you really weren’t familiar with. There were some processes and some philosophies around the times when you took that proverbial jump off the cliff. Could we start there and talk about some of those processes?

Waldo: Absolutely. I know many of your listeners are experienced professionals, sales managers, project managers, engineers, whatever, looking to revamp a new career to start something up. I’ll tell you the first thing that I did when I decided to leave the military and go into the business world and then become a speaker was to find a mentor, to find somebody who had been in my shoes, preferably ex-military, who successfully navigated that terrain into the business world. I searched. I asked for help. I talked to people. I found a gentlemen in Atlanta who became my coach and really inspired me to get into the business world and gave me a lot of great advice and professional networking tips. You just can’t execute without having that plan and having somebody to coach you along the way. If you’re afraid to ask for help, if you’ve got to do it on your own, then that’s a challenge.

I think you have more of a chance at success seeking out a mentor and then also joining an association of some sort that has the type of people who were doing what you’re doing. I joined the National Speakers Association when I decided to become a speaker. I read the books. I attended the seminars. I nurtured relationships with people who coached me who I now coach, who I now support and provide a counsel to. When you’re around that energy and connect with people, find out what they’re doing right or wrong be it in technology, in social media, whatever it is, you’re off to a great start. It involves humbling yourself, being the type of person that realizes they can’t do it on their own. I think it was a very important factor in my success.

Vera: When you were out making those connections and nurturing relationships and all of the information that you were gathering, I would imagine that it could be somewhat overwhelming. How did you keep track of all that professional networking information?

Waldo: Oh, goodness. You’re exactly right. It is overwhelming. I was in sales and marketing before, so I had a job. I get up at 7, 7:30. Be in the office by 8:30, 8 o’clock, whatever. I’d work until five. I hit the gym and this was before I was married because I’ve been married six, seven years and I have a little six year old that I mentioned to you. I was totally committed to my job. I was making a lot of money in sales and then at night from nine to one in the morning, I was building my business. I was learning the speaking industry. I was listening to the tapes, going to the websites of the best speakers in the world, following what they did. I invested the time. You’ve got to get like a PhD, a mini PhD or a mini MBA, in your profession. You have to go to school on it. If you’re currently working, you’ve got to find the time.

You’ve got to turn off the TV and be maniacally focused on taking control of your education. Yes, it was overwhelming, but that’s once again why my wingman, the men and women who helped me and supported me and coached me, I would bounce ideas off of them. I would talk to them and say, “Hey, what’s working? What isn’t? Help me shorten my learning curve so that I don’t make this mistake and using this piece of software that was recommended to me from this vendor, but I see you guys or gals possibly use it. What do you have? What device do you have?” Getting that reference from other people who are in the trenches from you or in the trenches with you and have been there, done there, could shorten your learning curve. Prepare to be overwhelmed. It’s just part of the entrepreneurial battle.

Vera: Whenever you had done all of that professional networking, et cetera, and you have successfully jumped from the military to corporate America, from corporate America to being a professional speaker and people come to you for advice, are you talking to them about the things that didn’t work so well for you as well?

Waldo: Oh, yeah. Absolutely. I probably should have for example hired an assistant sooner. I should have invested in that, somebody who can help alleviate some of the logistics and brain power necessary to run a business. I should have went to more of the meetings. I went to some of the NSA meetings, National Speakers Association meetings, but they also have workshops and seminars that I wasn’t able to attend because of my schedule. Also I think it’s important to be involved in other groups of like-minded business individuals that aren’t necessarily in your profession. Call it a Mastermind group. Call it going to a Chamber of Commerce meeting. Joining some associations. I did not join those and I should have. You don’t want to be around your clones always as you’re evaluating your future.

One of the most important professional networking tips I could give your audience is that you want to be around other successful people who may have an acumen in financial services or accounting or technology or whatever that can help supplement and augment your weak areas. You could provide them insights and your strengths. Does that make sense?

Vera: Mm-hmm (affirmative). It absolutely does.

Waldo: Reach out to other groups of people and don’t just hang out with other clones. I think it will help broaden your perspective not just in your profession, but in the business world in general.

Vera: Waldo, that’s interesting because this very podcast is really devoted to that because I have a wide array of guests on the show and all of the systems or the processes that they use absolutely go across any industry that you’re working in.

Waldo: Yeah, totally. Totally. That’s why I was on the phone yesterday with my accountant and sharing certain things about investments and this and that and real estate. Having that professional network of people and getting out of your … I always say, “Think outside the cockpit.” Broaden your insights and perspectives and don’t think somebody who isn’t in your profession can’t be of assistance to you. I also think in that same regard, one of the reasons, Vera, why I have been successful is that I coach a lot of other people. I spend time inspiring, mentoring, giving advice to folks who are either my peers or folks who were struggling. I believe when you put that energy out there and you help others … I talk about being a wingman.

I mean if I’m not one of my personal life and if I’m just philosophizing about it in my books and on stage, I’m not true to who I am. I think it’s important to lend your wings to inspire, to help, to lift others up in the process of you reaching your hand up to be lifted up. You always need a hand up on the ladder of life and a hand down to lift others who need your advice and experience and lessons learned to help them take it to the next level.

Vera: Oh, I love that. That’s a great analogy too because I find myself mentoring and doing the same and it really comes back around. It’s very interesting.

Waldo: In that same regard, I have a little bit of problem with this sometimes because I think most of us do. We have to be able to reach out and seek out a mentor too. I don’t know if you’re familiar with Gary Vaynerchuk?

Vera: I am.

Waldo: Goodness gracious. He’s all over the place. I have a connection with him. We speak at a lot of the same conferences. My friend Jeffrey Haslip is friends of him so I try to leverage him. I said, “Jeffrey, I want an introduction.” I was in New York City. I went by his office and I dropped off a copy of my book, a little note. We’re both Jews from Russia and from New York. There’s a lot of similarities there. I connected with him. I’m reaching out to him. We connected a little bit via email. Don’t be afraid to seek out somebody who’s a couple levels above. If you do it with respect, professionally, stay consistent, then they’ll eventually turn around. I think it’s incumbent upon us to not just help others, but to seek out help and realize that if we don’t ask, it won’t come. Right?

Vera: Exactly. Exactly. What drove you to write the book “Never Fly Solo?”

Waldo: The book is really a compilation of like a flight plan of some of the lessons learned that I’ve had in the military that I took over into the business world regarding preparation, regarding contingency planning, regarding building relationships and the professional networking tips I was given coming up in the business world. I remember when I was a young captain. I’d shoot out a lot of people. I was a typical New Yorker. I was some hardcore great fighter pilot that lacked the appreciation and compassion of the teammates who were on my team, the maintenance folks and all those other people, the wingman doing the job. Long story short, my commander made me go out on the flight line one day and spend a day in the heat of the summer changing tires and turning wrenches and working and fueling jets with the enlisted crew who I had no clue what they were doing.

They were means to an end for me. That’s just a lesson that I learned about relationships. That there are a lot unsung heroes who allow us to get the job done. I took all those lessons and I compiled them into the book and use that as more of a detailed flight plan for success in addition to my speaking. It also shares a lot of my personal struggles. We mentioned this before, Vera. I overcame a huge fear of heights and massive claustrophobia to become a fighter pilot and dealing with fear and being able to ask for help and turn in that fear into courage to take action is really the impetus to everything that I do in “Never Fly Solo” and my coaching programs and in my speaking.

Vera: Would you expand just a little bit on that claustrophobia fear?

Waldo: Yes, absolutely. For those that are listening, fear is a huge detriment to success. It’s just part of life though. We have a lot of people who are afraid to take action because they’re afraid of failure, afraid of rejection, afraid of looking stupid or whatever it is. It’s normal. It’s part of life. It’s about being human. Anybody that talks about fearless leadership in a speech or on a book title is just full of baloney. I don’t like the philosophy. It’s an unrealistic expectation. The key is to leverage that fear and to use it as a launching point to your success. As a fighter pilot, long story short, I’ll get into this a little bit. I was flying for three years as an instructor and I flew in the active duty Air Force for 11 years.

Three years into my 11 year flying career, I almost died scuba diving in the Caribbean. It was the first time I’ve ever been. My mask malfunctioned. I inhaled a bunch of water. Had a panic attack. The worst experience of my life. Got out of the water and said, “I’m never doing that again.” Just a few days later, I’m flying in the jet on a cross country flight from Oklahoma to New Jersey actually. There was terrible weather. Couldn’t see the sun. Couldn’t see the ground. I basically had that same panic attack that I did a few days prior. Instead of being 30 or 40 feet into the water, now I’m 30,000 feet in the air and realized I had claustrophobia. I’m like, “I got to get out of this plane.” You can image that feeling, the heart pounding. I don’t know if you’ve ever had a panic attack before.

Most people haven’t, but for those that have, it’s just absolutely overwhelming. Basically for the next eight years of my 11 years active duty flying career, a total of almost 3,000 hours, I had to deal with this fear, this phobia, of having a panic attack, wondering if it would impact my mission. The point is I didn’t quit because I loved flying jets and the thrill and the excitement greater than the fear. When you’re dealing with situations in your life where you have to take that jump off the proverbial diving point … By the way, to graduate the academy and become a pilot, I had to jump off a 33 feet high diving board which was also the next scariest experience of my life dealing with that bad fear of flights which I did jump.

You have to realize that to grow, to take life to the next level if that’s where you want to be truly, because I think some people want to be there in some way, but at the end of day they just want to be average and that’s okay. You have to be willing to take the leap to do which makes you comfortable to step outside of your comfort zone and to face those fears because on the opposite side of that fear is where growth is. That’s where life is. That’s where your next job opportunity, that’s where your next sale’s going to come from, that’s where your business is going to come from, your next relationship’s going to come from. Lord knows I got married at 42. That was that 100 foot diving board I jumped off of because it’s really about commitment. If you don’t love what you do, if you’re not willing to sacrifice for it, if it’s not getting you out of bed, nevermind what keeps you up, it’s what gets us out of bed that counts, then you got to find out what drives that in you.

For me, flying the jets, the thrill and the excitement was greater than the fear and I didn’t want to look back on my life with regret and that’s why I didn’t quit. There was a whole other reason why I was able to succeed because of my wingman, because of the people who encouraged me, my training, my health, my fitness. There were a lot variables that came into it. I wouldn’t be on this phone with you talking about these things and with the wonderful blessings that I’ve had in my life without … There was scars. Be willing to get those scars. That’s what builds character and creates leaders. If you’re not willing to get dirty in the ring and get shot at so to speak, then the business world and the entrepreneurial world isn’t for you.

Vera: Absolutely. I couldn’t agree more. “Never Fly Solo” is the book. You’ve given us some really good insight into the strategy or processes that you used to jump from absolutely two industries that were somewhat connected, but not really. I think that has been very insightful. Before we wrap up our discussion, what’s your next challenge?

Waldo: My next challenge is how to monetize my business outside of speaking. I speak all over the world 80 times a year. Fortune 500 companies from Siemens to Verizon. I just spoke for the Denver Broncos a few years ago. I was just in Saudi Arabia speaking for the second largest chemical company in the world. It’s really to take what I’m doing and put it into video to create coaching programs online so that I’m not on the road as much. Lord knows traveling could be a drag on any family, but I do provide so much more than just my keynotes and workshops that I do. There’s a lot behind it. Some of it we’ve shared. I want to do a lot more entrepreneurial coaching and do it online or on the phone and not have to travel as much. I’ve been working with that.

I’ve got a videographer. We’re going to do a lot more stuff on YouTube. Create a membership site. That’s going to involve some technology and some resources and tools which you’re an expert at, right?

Vera: Right.

Waldo: That’s going to be something that’s going to be challenging for me and I’m also working on my next book called “Wingman.” That’s going to be about mentorship and making tough decisions in life. It’s about a young man who has an opportunity to lead a team and he meets a mentor who inspires him to step outside of his comfort zone and take the road less traveled to grow as a leader and as a human being. That’s my next book.

Vera: Wow. I cannot wait for that one to come out.

Waldo: Thank you.

Vera: Please tell our listeners the best way to get in touch with you.

Waldo: If you want to learn about me and about my videos and get a little inspiration and motivation on entrepreneurship and sales and business development, if you go to YourWingman.com, YourWingman.com, you can go there and then you click through some pages. You can sign up for a newsletter. I’m all over social media. If you just google Waldo Waldman YouTube or Waldo Waldman Facebook or LinkedIn, I’d love to connect with you there. Just make sure you say that this is how we met through Vera. Then also I want to give you all a gift, a gift of my book, “Never Fly Solo,” which was a New York Times or Wall Street Journal bestseller. You can get the download, the audible download, on Audible.com for 19.95 and I’m going to offer it as a gift for you.

If you all want to go to YourWingman.com/NFS as in “Never Fly Solo” and pop in the word “wingman,” you’ll get taken to a site and you can download the book and listen to it after this podcast. Once again, it’s YourWingman.com/NFS as in “Never Fly Solo.” Password all lowercase “wingman.” You’ll get the book and enjoy it. Let me know what you think about it.

Vera: Waldo, that is great. Thank you so much. I know I will be one of the first ones to download that audiobook.

Waldo: Wonderful. You’re very welcome.

Vera: System Execution fans, no matter how many notes you took or how often you relisten to this episode, the key is every successful business use a systems to drive to a better outcome. Waldo, thank you so much for sharing your expertise and insight with our listeners today.

Waldo: You’re very welcome, Vera.

We hope you found this episode of System Execution on professional networking tips and mentorship to be enlightening. For free examples, case studies, eBooks and more, be sure to visit SystemExecution.com/resources. Contribute to the conversation by reaching out to Vera directly on email at Vera@SystemExecution.com. Until our next episode, thank you for the privilege of your time.




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