From broke jazz musician to $100 million in online sales… Jeff Lerner’s story and social media content have inspired millions to get control of their future and reshape their life around his “3 Ps of Success” (Physical, Personal, & Professional). After a decade of building multiple businesses to over 8 figures and landing multiple times on the INC 5000, Jeff turned his focus to building the world’s first institute of higher learning exclusively for entrepreneurs. In 2019 he founded ENTRE Institute, the fastest growing education company in the world, where over 200,000 students have studied how to grow a business.
In 2021 Jeff set his sights on solving one of his students’ biggest pain points and launched Entresoft which fast became one of the most popular small business software suites on the Internet. Jeff is also an active real estate investor with a personal portfolio nearing 8 figures. Jeff’s interest in entrepreneurship began in his 20s when as a pianist he was often hired to play in the homes of successful CEOs and business owners. In 2008, at age 29, after multiple failed ventures including a restaurant franchise that left him with a half-million dollars in debt, he found his first success online and paid off the debt in 18 months.
He currently maintains an active schedule of speaking events and media appearances while working day-to-day in ENTRE, hosting a top 100 business podcast, growing his YouTube channel, and working on his first full-length book “Escaping The Broken System” which is scheduled for publication by BenBella Books in Spring 2022.
He is married, an active father to 4 children, and still enjoys playing the piano for 1 hour per day…
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Table of Contents
Let’s start with a brief introduction first. Introduce yourself to our readers.
Jeff Lerner: I used to play piano for billionaires. They were all wealthy entrepreneurs whose lives seemed a lot more exciting than mine so I became an entrepreneur too.
Now a 3X INC5000 founder with $100MM+ in online sales and an 8 figure RE portfolio, in 2019 I started ENTRE Institute, the first institute of higher learning in the world for entrepreneurs and currently the fastest growing education company in the world. In 2021 I founded Entresoft, the world’s most complete small business marketing software.
Over 200,000 students now use my education and/or software to power their businesses and create their best lives!
Our audience is interested to know about how you got started in the first place. Did you always want to become a CEO or was it something you were led to? Our readers would love to know your story!
Jeff Lerner: Never cared much about being a CEO. Just wanted to do cool things and have a life that made an impact on more than just myself and my family. Playing small sounds boring and founders/owners/CEOs get to play the biggest games.
“Selfmade” is a myth. We all received help, no doubt you love to show appreciation to those who supported you when the going got tough, who has been your most important professional inspiration?
Jeff Lerner: A few fine folks:
My Dad – when I was in my early teens he left his successful career as an institutional stockbroker to open his own money management firm. After a couple of years of struggle it took off and I got to see the upside of ditching our comfort zone, taking a risk, and making it work with grit and grind.
My Mom – one of the first female partners at a Big 5 US law firm she had to outwork and outcharm her male counterparts every single day. She showed me that intellect is power but intellect plus empathy is a superpower.
Bruce Johnson – inventor of the BreatheRight strip (and brand). Bruce is a friend I made through an unlikely encounter (he was in the audience at a premiere of a musical I wrote in college) who became a mentor and friend throughout my 20s and still to this day.
Larry Goldstein – business manager for Todd Wagner (a Dallas billionaire/Mark Cuban’s business partner in broadcast.com). Larry put some personal money into one of my early ventures then matched it 10 times over with advice. Larry taught me what “real” business dealings are like – expectations are high, preparation is mandatory, and respect is earned.
The billionaires I played piano for – they showed me that outsized success is possible and not just reserved for giants or superheroes. They were all surprisingly down-to-earth or at least showed signs of being mortal. 3 key partners:
Matt Whitney – my first (and one of only 2) successful co-founder relationships. Our business didn’t take off but we grinded together for years and I learned the special kind of brotherhood that can come from building a business together.
Amber Lutui – started as my personal assistant and ended up as COO and running my digital agency with little input from me for multiple years. Until I worked with Amber I never knew the power that comes from fully trusting and empowering the right someone to multiply your efforts.
Adam Whiting – my current business partner who has humbled me by showing me that my combination of intellect and work ethic are not unique.
How did your journey lead you to become a CEO? What difficulties did you face along the way and what did you learn from them?
Jeff Lerner: I became CEO by default – once I founded a business someone had to run it! I’ve been CEO of every business I’ve had (4 officially, a dozen unofficially) and gotten better each time. It basically went in 3 phases:
- Phase 1
Focus on sales, marketing, business development, generating revenue, etc. Did ok but could never scale much beyond myself.
- Phase 2
Started learning management and operations (aka hired a coach) and learned to create workflows and organizational charts that worked (but weren’t amazing)
- Phase 3
Did a TON of therapy for personal reasons and learned soft skills like empathy, responsive listening, energy reading, the art of enrollment, etc. TBH I’ve pretty much had the Midas touch since becoming a softer, kinder, more compassionate person.
Tell us about your company. What does your business do and what are your responsibilities as a CEO?
Jeff Lerner: ENTRE Institute is an online education company that’s on a mission to disrupt the education system and usher a new generation of ‘ENTREpreneurs’ into the world. We provide our students with the complete ecosystem they need to learn how to become successful entrepreneurs, including digital courses, coaching, business accelerators, community, software, personal development events, and more.
As co-CEO, I am responsible for developing and communicating the large-scale vision and being the lead brand ambassador in the market. My co-founder/co-CEO partner is the day-to-day operational CEO.
What does CEO stand for? Beyond the dictionary definition, how would you define it?
Jeff Lerner: In ‘Less Is More’ Jason Jennings says roughly “You’ll know you are doing an effective job as CEO when your team starts rolling their eyes because you talk so much about the mission, vision, and values of the organization.”
I believe this is my skill – to hold a vision and defend it against the dual nemeses of market competition and human insecurity. I am weak in a lot of areas but this strength, along with a deep love and respect for the amazing human beings I work alongside, engenders loyalty and hard work, which are the key to weathering the hard times that do most businesses in.
When you first became a CEO, how was it different from what you expected? What surprised you?
Jeff Lerner: The realization that technical skills are the least important element of leadership (except in sales – it is hard to lead in sales if you are not recognized as a skilled salesperson).
There are many schools of thought as to what a CEO’s core roles and responsibilities are. Based on your experience, what are the main things a CEO should focus on? Explain and please share examples or stories to illustrate your vision.
Jeff Lerner: I am a believer in the dual leadership roles of visionary & integrator (as laid out in the book Rocket Fuel). I think a CEO needs to make sure that both of these bases are fully covered and know him/herself well enough to know where he/she is strong and where help is needed.
Personally, I am a strong visionary and a decent but unexceptional integrator. Thankfully my business partner is a strong integrator as well as a decent visionary (he’s probably a better visionary than I am integrator lol). Together we function essentially as co-CEOs that form what I consider to be a complete CEO unit with equal strength in vision and integration/execution.
I realize our situation is fairly rare and it works well in part because we are also equal partners in and cofounders of the company. That said I think every CEO needs to make sure that the vision and integration needs of the business are equally well-tended to which is almost always going to require a creative approach since few CEOs will ever be extraordinarily strong in both areas.
Share with us one of the most difficult decisions you had to make for your company that benefited your employees or customers. What made this decision so difficult and what were the positive impacts?
Jeff Lerner: In 2 years ENTRE Institute grew from a team of 9 doing barely 6 figures a month to a team of 150 doing over $5 million a month. That type of growth creates constant pressure to level up as individuals and as an organization. Organizationally we have pushed hard to install systems and processes to support who we’ve become and prepare ourselves for more growth ahead but this rapid maturity has been hard on a lot of people. The company we were and the company we are/are becoming call for and reward drastically different types of behavior and many of the people that were with us when we started have not been able to transform or keep up (or been willing to).
Several people I cared about and without whom we would not have launched have had to be let go. In the end, I know it was best for all parties, and usually, deep down they did too, but at the moment it is painful for people to see a company that is thriving outgrow them and have to leave them behind. In most companies that grow at a more normative pace, people have time to evolve but we have grown so fast there just wasn’t time to wait on people to develop. As we know come out the other side though of rapid and intense maturation and leveling up process it is obvious it was the right move.
Millions of people are going to be impacted by the work we are doing and everyone here now knows it which creates energy and momentum that would have been impossible if we were still carrying the weight of our legacy players.
How would you define success? Does it mean generating a certain amount of wealth, gaining a certain level of popularity, or helping a certain number of people?
Jeff Lerner: Success for me is being able to create a fulfilling life while making a positive impact. I spent years building businesses with the goal of making money and taking good enough care of the customers to maintain a good reputation but service and value were not obsessions until 2018 when I started planting the seeds of ENTRE. Since what in hindsight was a bit of an early-midlife crisis I have been obsessed with doing work that really matters in the world and tackles the big human challenges I see around me head-on – and I am finally fully fulfilled (and not coincidentally also making more money than ever before).
In short, I used to think making a profit was the primary purpose of business while serving customers was a thing you must do to support that purpose. I now realize that serving customers (ideally in the biggest and most important ways possible) is the primary purpose of business and making money is the thing you must do to support that purpose. Thus I am finally successful.
Some leadership skills are innate while others can be learned. What leadership skills do you possess innately and what skills have you cultivated over the years as a CEO?
Jeff Lerner: Innate: Intelligence, Verbal Ability, Work Ethic.
Cultivated: Empathy, Vulnerability/Authenticity, Humility, Compassion/Agape, non-Verbal Communication, Performance/Presence, Organization, Planning, Punctuality.
How did your role as a CEO help your business overcome challenges caused by the pandemic? Explain with practical examples.
Jeff Lerner: We built our business to address challenges that already faced humanity before the pandemic started but which the pandemic exacerbated. The “American Dream” has been deteriorating for decades and people now are being overcharged for education, undercared for by employers, and generally misled by banks and financial services companies regarding retirement. The birth-to-death roadmap we were given (school, college, job, retirement) is insolvent and what isn’t taught at an early age are the things people really need now – creativity, discipline, salesmanship, individual responsibility, strategic thinking, risk tolerance, etc.
Entrepreneurs are the lone subset of society that’s actually equipped to deal with the world now as it is yet mainstream society (pre-pandemic) still viewed entrepreneurship as too risky for most. On the contrary, I believe over the full length of a lifetime not being an entrepreneur is too risky for most, The pandemic shined a light on many of these issues and we have benefitted from “The Great Resignation” that ensued.
Do you have any advice for aspiring CEOs and future leaders? What advice would you give a CEO that is just starting out on their journey?
Jeff Lerner: Be obsessed with excellence across all areas of your life. Got emotional baggage? Heal. Got health issues? Take better care of yourself. Got relationship issues? Get therapy. Got time management issues? Get a coach. And so on…
Don’t be complacent or settle for the person you’ve become through experiences you didn’t choose. As the world gets more crowded it’s the people with the best energy that attract the best talent and outcomes. Be a great person to get great results.
Thank you for sharing some of your knowledge with our readers! They would also like to know, what is one skill that you’ve always wanted to acquire but never really could?
Jeff Lerner: Speaking French fluently.
Before we finish things off, we have one final question for you. If you wrote a book about your life today, what would the title be?
Jeff Lerner: I am writing that book (pub date May 2022, BenBella Books) and the working title is “Escaping The Broken System”.
Jed Morley, VIP Contributor to ValiantCEO and the host of this interview would like to thank Jeff Lerner for taking the time to do this interview and share his knowledge and experience with our readers.
If you would like to get in touch with Jeff Lerner or his company, you can do it through his – Linkedin Page
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