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Jake Wiley: “Rich dad poor dad”

Assuming that we all have the same 24 hours in a day, which we do, everyone you meet or are in contact with likely has had interesting experiences and or goals. Take the attitude that anyone you meet could be a future friend, partner or customer. It will change your life. This doesn’t mean that […]

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Assuming that we all have the same 24 hours in a day, which we do, everyone you meet or are in contact with likely has had interesting experiences and or goals. Take the attitude that anyone you meet could be a future friend, partner or customer. It will change your life. This doesn’t mean that you have to like or try and force something that is not there, but most of us start from the point of view that other people are strangers until proven otherwise. How many times have you known/known of someone for years only to be surprised to learn more about them and be blown away in some fashion. The more you circulate around people you keep at an arm’s distance the harder it becomes to get to know them. Start from a place of openness and you don’t miss those opportunities.

You can always decide that the relationship is not a good fit when you get to know them a little, but you are missing out on some amazing connections if you don’t give it a chance.

While probably obvious but others are attracted to people that are open, so it has an exponential effect on your network.


As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Jake Wiley.

Jake Wiley is an entrepreneur, CPA, former CFO, and heads client relationships in multiple regions at PwC. Jake has nearly two decades of professional experience building businesses, solving problems, and implementing solutions. At PwC, Jake has a distinct opportunity to provide multiple lines of professional services from the perspective of someone who has experienced sitting across the table as a C-level executive at numerous privately held companies. Before his work at PwC, Jake was the founder at Solar Inverted LLC, a Louisiana based Residential Solar Finance and Installation Company, which was later acquired by Palmetto Group, where Jake led strategic initiatives until late 2018.


Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

If you’ve ever seen the movie Slumdog Millionaire, where the seemingly random events and circumstances of life put the main character Jamal Malik in the position of being a millionaire when all of the events add up to an unbelievable opportunity, I’ve had so many experiences thus far that prove out that’s how life really works. While not culminating in the opportunity to win a game show for millions of dollars, the opportunities have been more than abundant.

I grew up in Atlanta, the product of parents that didn’t go to college and hoped for more for me. I lost my father early at the age of 9 to cardiovascular disease and was forced to grow up a little quicker than my mother would have wanted and learned early on I was going to have to figure out how to make it in life and if I wanted to give back to my Mom for all the sacrifice she had to deal with to raise me on her own I was going to have to make something of myself.

Early on in Elementary school, what seemed like a blessing, but turned out to be somewhat of a curse is the fact that I was identified as gifted. School wasn’t overly difficult without having to apply myself, and since I was in the gifted program I thought that I was applying myself. The reality is that I didn’t try much early on in school and in hindsight I was a pretty mediocre student.

Entering high school I was challenged for the first time academically when on the first day of school my math teacher told the whole class that she was the most difficult teacher in the school, that she would challenge us and a large portion of the class was going to earn a C grade and have to repeat again the next year and that would set our academic future forever. I distinctly remember looking around the class and being able to “do the math” from my peer group and I could actually identify a portion of the class that I actually knew had always outperformed me in years past and thus based on my existing performance I would be in the group that was going to repeat. She said the only path to success was to commit to an hour of homework for math each night and it would start to click. I decided then and there that I would at least commit the hour each night because that was within my control. Fast forward to the middle of the year, I was in the top 5% of my class and not only that, but I found that it felt extremely good to work hard and find the resultant success. As a matter of course, it was a breakthrough for me that taking extraordinary, but not unsustainable, effort could have such a dramatic impact.

(Me, Jake Wiley, in high school)

The next year, I transitioned to a highly academic private high school in town on a scholarship. During my orientation, my new academic advisor pulled me aside and told me bluntly that my chances of success in the new environment was stacked against me and that I needed to plan on 3+hours of homework every night just to keep my head above water and try and keep pace with my peers that were academically ahead of me. Coming out of the public school system during the sophomore year of high school was about the hardest transition there was and being a private high school there were no safety nets for me. Taking the success from the previous year, I decided I could at least commit, but as the saying goes I was scared straight here. I could actually fail out of a school! Coming from a home where neither of my parents had attended college and I was academically farther along than my mother had ever gotten in school at this point, whereas my peers almost all came from two parent college educated homes; I knew it was up to me. Fast forward to the end of the year, I made some great relationships at my new school, was welcomed into the homes of some of the most successful families and was able to break bread and have conversations with industry leaders, the parents of my friends who I believed were the unfair advantage my friends had on me. It hit me like a ton of bricks one Saturday morning when I was sitting at the breakfast table with a friend’s father just talking about life, concerns, goals etc. that he was a normal person just like me and that his success was driven by the secret that I had learned recently that sustainable extraordinary efforts create exponentially better opportunities. There wasn’t actually a glass ceiling that someone like me couldn’t break through, only self-imposed limitations. It was the most unbelievable realization and by the end of the year, I had won awards for math and physics as well as the dean’s award for standout performance by a male sophomore. I was so blessed to have been challenged significantly twice in my high school career because it changed the way I saw the world every day since and was the foundation that I could choose the life I wanted to lead vs. accept what seemed the norm.

It took nearly another 20 years to learn the other half of the equation, which is that what you are truly able to accomplish is dependent on how well you bring together others to move your goal forward.

After years of just getting by owning my own business it finally dawned on me that two things were missing.

  1. I could burn the candle at both ends and work 18 hours a day, and while the results were getting better with time, they weren’t anything near the vision of the success I had imagined. Even with the best systems money could buy, I would still need to be able to bring others into my journey.
  2. I needed to be able to sell myself and my vision in such a compelling way that brought out the best in others.

At the time I happened to be reading “Rich dad poor dad” by Robert Kiyosaki and he mentioned that one of the best things he did and recommended was go to work for a world class sales organization. You some of the best of both worlds, of entrepreneurship being that you ate what you killed and also had the support and training of a well proven machine. I decided that to try and fill in the two missing pieces of my business acumen I should work for a world class recruiting firm. I would get the opportunity to interview both candidates and amazing employers every day and learn how to sell myself first, build relationships, motivations and make the right matches. I’ll admit that being a recruiter wasn’t in line with my life’s ambitions, but the year and a half I spent in the seat pounding the phone, making cold calls, building rapport etc. was one of the toughest and best years I’ve had professionally. It also proved uncategorically that you can be an entrepreneur and align yourself with the best brands and have an extremely symbiotic relationship. Most people think being an entrepreneur means striking out alone and trying to beat the big names. Ultimately every entrepreneur is selling themselves to their prospects. People buy you, not your company, but the credibility you add by your associations might be the difference between getting to pitch or not.

The culmination of all these experiences has led to the discovery that the inability to bring others into your vision and providing a compelling reason for joining forces is almost universally what keeps business from breaking through to real success. Wiley on Business is a platform and podcast that focuses on helping entrepreneurs and business owners make the transition from an inevitable burnout into a company that can carry the vision to exponential levels. Since humans have always learned best through the power of storytelling, Wiley on Business focuses on sharing stories from successful entrepreneurs that have made the breakthrough from a struggling small business. Every story brings its own unique nuggets of wisdom, but the diversity in the experiences should allow everyone to find themselves and their journey in the stories and gain a first hand account of how the transformation was made.

Can you tell us a story about the hard times that you faced when you first started your journey?

When I left PwC after nearly 7 years working for a large company, I found myself truly on my own. No-one provided me with a computer, internet, office support, printers, phones, and most importantly a guaranteed paycheck. Nobody can prepare you for the feeling of going out on your own until you get there. Its a romantic idea of striking out on your own when you have a paycheck and think you can do better, but there are dark days of doubt when you are responsible for everything. Time becomes so distorted, whereby the days can’t go by fast enough to get to the next appointment or opportunity, but the days also go by so fast when it comes to invoices, mortgage payments coming due.

Overnight I went from a promising employee at one of the largest service organizations in the world to a nobody in the world of business. Everyone from my wife to our extended family looked at me/us like we were crazy, waiting for things to implode and it was completely overwhelming at times.

Where did you get the drive to continue even though things were so hard?

It might be silly but three things helped me along the way.

1) I would look around and others that were successful on their own and I’d try to make an honest assessment of whether they were better in any way than I was, and would try to take anything I could from that assessment and implement it in my own business.

2) I would listen to/read any book, webinar, training I could get my hands on that talked through both the strategies for running a business and the mental aspects of getting it all together.

3) I would take the lessons learned in high school and figure out how much work it took to be average/moderately successful and simply do more.

At the end of the day, I had a family to support and there was no choice or fallback plan.

So, how are things going today? How did grit and resilience lead to your eventual success?

Having learned some great lessons early on in life about persistence, extraordinary but sustainable effort gave me a north star that I could always turn back to when things didn’t seem to be going as I had hoped. I’ve adopted the personal mantra that “Life is going to be hard, I can either deliberately choose what obstacles I want to overcome or I can let others choose for me. I choose the former.” I’ve had the opportunity to build amazing relationships, align myself with the best partners and brands and share the message via the podcast and every day is a step forward.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I had spent several months proposing on a large contract with a group that I thought was going extremely well and we were in the final stages of clarifications to get the document in the hands of the lawyers as we had bested our competition. I was scheduled to have a conference call with the counterparty and was expecting a few brief formalities and a short quick summary of the transaction and off to celebrate. I’d flown across the country for a series of meetings, one of which was with the CEO of this company to officially “break bread” and formalize the new relationship later in the week. Instead, the counterparty was extremely curt and to the point that there was pretty much no way they would ever do business with us, we didn’t know what we were doing and that officially concluded our relationship. I expressed very professionally that I did not understand where he was coming from or what had happened, but that I respected their decision to go another direction. It was a sucker punch, and my partner at the time was watching me from across the way while I was on the call and immediately ran over and asked what they hell had just happened as they’d never seen me look so confused before. I relayed the message I received and we stared at each other until my phone started ringing.

It was the counter party calling back. Apparently today was the day they were telling the parties that didn’t win the engagement they were out too. He’d had to psych himself up for the calls and was so focused on delivering the bad news especially to one party they’d uncovered some unsavory information late in the process and he’d felt like a ton of time had been unnecessarily wasted that he didn’t realize that he was talking to us first and gave us the practiced take a hike speech. He was unbelievably sorry, hoped that we’d understand and hoped like hell we’d consider working with them considering how we’d just been treated, which of course we were! After a well needed laugh everything was back on course.

The lesson was that I could have reacted with equal vehemence and tried to make a point, but instead I clearly stated that I did not understand his perspective but respected their decision nonetheless. Had it been a test to see our true colors when the chips were down, we would have gotten high marks. When he called back to apologize and beg us to consider working with them, their esteem for our team was at a new level because of the professionalism with which we responded and while a mistake they knew we’d be able to communicate if and when challenges arose during the lengthy engagement.

What do you think makes your company stand out? Can you share a story?

Taking into consideration what it’s taken decades to learn the message I deliver in the podcast, what makes you stand out is that it’s not about how great you are but how much more value you can provide to others. When I wake up in the morning, what makes me excited about what I am going to do is helping others get out of their own way, focus on what’s important and make some real breakthroughs.

Just this past month, I was speaking with a prospect that had come to us with a preconceived idea of what he wanted to do. We were able to listen to what the client thought he wanted, then started peeling the layers back to discover the real end objective and the clients overall concerns which were significant enough that I am not sure they would actually get off the fence to take action. We’ve all been there, you know something needs to change, but you can come up with millions of reasons to keep thinking about it and nothing actually happens. These are the things that eat at you and keep you from making breakthroughs. Putting the right people on the call from our side, we were able to identify the root issue and were able to come up with a solution that was totally digestible, a lot less risky and one the prospect was able to say on the spot that he was ready to proceed. In addition we got a heartfelt thanks for listening and bringing an option that was immediately actionable. What he was actually thanking us for was the breakthrough that occurred. We were able to turn a mountain into a hill and they immediately took the first step on the journey they’ve been talking about for years.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Be clear on where you want to go and take steps every day that are pointed in that general direction. Create easy wins every day, even if it’s one email, phone call or to-do list item. Don’t try to eat the whole elephant every day. Most days if you get your easy win out of the way early you end up with momentum that helps you take a few extra steps.

When you know where you are going and your small victory steps each day you will find that you are much more intune for conversations, discussions, chance encounters that can help you along the way. When you are in the eat the whole elephant mode, you don’t even know where to start and it takes over your whole mind and you miss all the opportunities that surround you and it’s no fun. If getting out of bed or getting started is work or hard on its own, you are doing something wrong. Make the first step or success of the day easy and get momentum going for you, then you can tackle that challenge item for the day.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Tony Jordan was the dean of boys at my high school who saw something in me when I applied as a sophomore and essentially pushed my application through ensuring my acceptance. Interestingly I had no idea of any of this until the end of the school year when he called my mother to tell her that I was going to be awarded the dean’s award that year and why that meant so much to him. I actually thought that he had thought my acceptance was a mistake because he was always watching closely. Little did I know that he WAS watching me closely and cheering me on behind the scenes and following up on me with teachers and other students.

While I was appreciative at the time, looking back several decades later the profound impact his decision to take a chance on me meant all the difference in the world and I am eternally grateful. In fact, I think his actions to put me in an environment where with hard work I could actually thrive carries on with what I am doing today, helping others realize their real potential.

How have you used your success to bring goodness to the world?

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

  1. Don’t start with an attitude of you against the world and you have to be this independent entrepreneur making waves. When you align yourself with great names and brands your credibility goes up.
  2. Require yourself to give more value than you receive. If your counterparty feels the transaction is more than fair, you have a partner and the relationship can weather the ups and downs that will inevitably come with any relationship over time.
  3. Don’t try to be everything for everyone. If you don’t resonate with what you are doing for someone else it won’t work. It’s better to give up short term gains for continued depth. This is SO hard to do when opportunity is staring you in the face.
  4. Build and seek out new relationships every day. You never know where your next partnership will come from, but you’d better believe it will be based on a relationship. The more and better relationships you have the more opportunity.
  5. Number four is so important, it’s worth repeating.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Assuming that we all have the same 24 hours in a day, which we do, everyone you meet or are in contact with likely has had interesting experiences and or goals. Take the attitude that anyone you meet could be a future friend, partner or customer. It will change your life. This doesn’t mean that you have to like or try and force something that is not there, but most of us start from the point of view that other people are strangers until proven otherwise. How many times have you known/known of someone for years only to be surprised to learn more about them and be blown away in some fashion. The more you circulate around people you keep at an arm’s distance the harder it becomes to get to know them. Start from a place of openness and you don’t miss those opportunities.

You can always decide that the relationship is not a good fit when you get to know them a little, but you are missing out on some amazing connections if you don’t give it a chance.

While probably obvious but others are attracted to people that are open, so it has an exponential effect on your network.

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