As a part of our series called ‘Five Things I Wish Someone Told Me Before I Became A CEO’ we had the pleasure of interviewing Michael Simpson.
Michael Simpson is a corporate intrapreneur turned three-time entrepreneur. As the chairman and CEO of PAIRIN, the Workforce Journey company, he works to bridge the opportunity gap for future generations by personalizing career exploration, job matching and professional development. Michael founded PAIRIN and built it from the ground up.
Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
I grew up in a multiracial family that struggled with a lot of abuse, multiple divorces, daily financial strain and bankruptcies. I dropped out of community college to work four jobs to support myself and my family. Because of my non-traditional path, I faced many challenges and lessons that have helped me grow and relate to those who are disadvantaged and facing similar hardships. Thanks to the support from mentors and role models I met along the way, and a passion for developing my own skills, my life and career became one I chose, rather than it being defined for me. After a decade as a certified coach I decided the best legacy I could leave would be helping the alongsiders — the coaches, counselors, workforce professionals — by building software that connected the people they serve with the career, education and services to help them along their journey.
Can you share the most interesting story that happened to you since you began leading your company?
Several years ago, we took an enormous gamble with the future of our company by pivoting and accepting a very large contract with a state that had no funding associated with it. We agreed to the commitment, then had to help them raise the funds to pay us. It could have bankrupted us, but our team rallied. Not only did we help raise the funds, but we shipped on time and even launched in two states on the same day. Since then, our entire growth has been built upon that one gamble I made on our incredible team that paid off. There was a lot of doubt and many thought we couldn’t do it, but we made it happen and now wonder what other “impossible” things we might be capable of.
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?
Most of my mistakes didn’t make me laugh at the time but are funny now! When I had the initial idea for this business, I contacted a former employee who at the time was doing a lot of venture capitalism for a large company. He set up meetings for me with top investors in Silicon Valley. At the time, I had no idea how to build a pitch deck and showed up at one of the two largest VC firms in all of California on two different days. The very first pitch was rough — I got about three minutes into it and one of the VCs did a typical thing and said, “I don’t have any idea what you’re talking about.” Within seven minutes he was berating me in the most prototypical VC style you could imagine. From there, out of pure panic, I adjusted my entire pitch on the fly instead of saying, “I don’t think we’re a fit for your portfolio”, or just asking questions. The presentation was scheduled for 30 minutes and by 12.5 minutes it was over. I left defeated and thought I just wasn’t cut out for entrepreneurialism. Thankfully I didn’t quit, but I wonder how many great entrepreneurs have, due to similar experiences. My friend helped me with the original deck, but I should have asked for more help and done more homework. My takeaway from the experience was to get as much feedback as you can from as many people as possible and never trust one person’s opinion — even one investor. I worked through the night and went to the next VC meeting nervous but better prepared. They told me my presentation was a 7/10 (progress)! I received great feedback and learned a lot from that meeting. I also learned that not all VCs are jerks, and I should partner with the ones that want to help entrepreneurs, not just themselves.
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 about that?
There are a lot of people I am grateful toward. I would say the first one on the list is the most helpful investor I’ve ever known, Victoria Fram. She was with Village Capitol at the time, which had a unique investment model based on putting entrepreneurs first and allowing entrepreneurs in their accelerator to select the fund’s investments. We were accepted to their accelerator program and they have invested three times. Anytime I have struggled with anything investor related, I have always been able to pick up the phone and get her perspective and advice. Every great investor we have came from relationships with Village Capital. I cannot thank them, and Victoria, enough.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?
A CEO has to understand everything — but does almost none of it. They need to be able to give people direction and to help them succeed, but not actually do their work. Perhaps the biggest thing a CEO has to learn is when to let go and delegate, and when to let people fail and define what failure is. Too many people focus on success rather than what is an acceptable level of failure to drive professional development. That should be true of all leaders, but CEOs have to be really good about it and most aren’t, because their ego gets in the way. Sometimes you have to assign a job to an employee you know won’t do as good of a job as you, so when they fail, they will truly understand what is required. But, you have to be there to help them process the experience so they won’t repeat it. Not a ton of CEOs do that and it stunts the growth of their team and company. Every CEO is also constantly figuring out which job they are next going to fire themselves from. Delegate, watch the process (and maybe the failure), teach, coach, encourage then repeat. And keep the Pepto Bismol on your desk, because this is heartburn inducing stuff..
What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?
This will not be a popular answer, and I’m not talking about CEOs who step into a successful company, but I have to say that the biggest myth is that Founder CEOs get paid too much. If they are an entrepreneur CEO, they likely went years mortgaging their own homes, making no money, convincing their spouse to give them “just six more months”, emptying retirement accounts, etc. People more often than not believe once a CEO is actually making a good salary that they are making too much. What they don’t take into consideration is what that founder sacrificed along the way to build their company, which includes retirement benefits, the salary they sacrificed if they had worked for someone else, and the years of sweaty terror their whole family endured. Successful companies are more stories of endurance and survival until they get it right, than glory. But nobody sees that.
What is the most striking difference between your actual job and how you thought the job would be?
I thought I would spend more time running my company than working with investors. The most challenging part of my job is raising funds, dealing with expectations of people that often don’t take the time to really understand your business and prospects. This problem is my fault. If I knew then what I know now, I would’ve waited a lot longer before I brought in investors and then been in a position to be very selective about the money I raised.
Presumably not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?
The type of person who is afraid to fail or needs to take credit for success shouldn’t be an executive, an entrepreneur or a CEO. CEOs should constantly be pushing credit to others. I think what you need to have is cautious trust. You need to be willing to give someone a chance based on their potential, that sometimes they don’t even see. But when they fail, you need to be able to hold them accountable in a way that doesn’t break their will or break your company. One of the biggest problems with managers and executives is their willingness to have hard conversations, hold people accountable to high standards and not keep moving the goalposts, especially in today’s society where a lot of people are afraid to challenge. There must be consequences for poor performance, but it needs to be balanced with an equal emphasis on praise. Employees need to know how success is defined for the company and most leaders fail in that area. Many executives want to be liked, but what develops deep trust is helping people become better versions of themselves. I’m constantly working on being better at praising progress, which is a challenge for someone who is always looking for what can be improved. Know your weaknesses and never stop developing. You’ll be the example that will motivate your team to develop.
What advice would you give to other business leaders to help create a fantastic work culture? Can you share a story or an example?
Have your employees define it, don’t try to figure it out yourself. We’ve always worked with our employees and their families to define what a fantastic work culture would be for them, and then worked together to see it become a reality. In fact, as our employees return to work, we’re putting together a workshop for a few days to define what an ideal post-pandemic workplace is to them so everyone can contribute to the next phase of our company. It shouldn’t be a top down decision, especially early on. It’s always a work in progress to keep a fantastic work culture.
How have you used your success to make the world a better place?
I created my company to make the world a better place so everyone’s life journey would be relevant and equitable. Everything we do is to help those in the greatest need of government services, education, guidance and coaching get that in a personalized way.
Fantastic. Here is the primary question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
- Avoid outside investments as long as possible.
- When you do solicit investors, choose wisely.
- You don’t have to work as many hours as you think you do, so don’t forget to live a happy life.
- There are a lot of people willing to help if asked.
- Don’t assume the quality of relationships you have today will be the same in the future, so put everything in writing.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
I would transform our education system to focus on teaching and developing skills that matter. I would also change the hiring processes with businesses so they focus on the skills they actually need, not on the degrees that may be irrelevant.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
It is a lesson which all history teaches wise men, to put trust in ideas, and not in circumstances. –Ralph Waldo Emerson
Every great accomplishment was once an idea that others scoffed at and mocked. Everything that seems normal today was once “impossible.” It is a person’s belief in an idea that begins everything worth doing. I believed in the idea of what PAIRIN is becoming when literally nobody else did. Nobody understood the vision. It took me a long time to form it in my mind, articulate it and develop a path to get there. For some reason, a lot of people believed in me before the rest of that was clear, but that is always the way. it will always be the case that the belief of others in your vision will be less than yours. It has to be. Don’t let their lack of belief keep you from your dream. The more you are all in, the more others will join you..
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them
Lawrence Brooks — he is the oldest living veteran in the US. It would be fascinating to learn what 111 years of wisdom can teach a person.
