In this episode: In the first episode of The Entrepreneur’s Adviser™, Jon Peyton explains why the show exists: so founders and senior executives can hear how others worked through the same struggles and know they aren’t alone. He then takes on the episode’s real question. When it comes to long-term success, which matters more: your personality or your mentality?
Key insights
- Entrepreneurship is, at its core, problem-solving. Senior executives face many of the same problems, because they’re often running a business inside a business.
- Harvard Business School’s ten traits of successful entrepreneurs run from curiosity and structured experimentation to persistence and long-term focus. Jon adds an eleventh: be a voracious learner.
- If you can’t accept failure, you’ll stay stuck in it. Jon’s motto is “fail fast, fail often, fail upward.”
- Traits can be learned, but mentality has to come from within. In Jon’s view, real success starts with mentality and grows with the right traits.
- The higher you climb, the more your success depends on the people around you rather than on you.
Episode timeline
- 0:24 Why this show exists: you’re not alone
- 2:27 Who Jon is and the ecosystem of firms he built
- 4:43 Why entrepreneurs and executives share the same struggles
- 7:20 Personality versus mentality: the battle in your mind
- 7:44 What Pretty Woman and Wall Street taught Jon about value
- 15:17 The ten traits of successful entrepreneurs
- 17:23 Structured experimentation: test, validate, iterate
- 19:50 Adaptability: evolve or die
- 21:09 Decisiveness, and why the smartest person in the room is in trouble
- 23:51 Risk management, and why it protects both your business and your health
- 25:36 Acceptance of failure: fail fast, fail often, fail upward
- 29:00 Innovation, price and value
- 34:38 Jon’s eleventh trait: be a voracious learner
- 36:36 Growth mindset: praise the process, not the talent
The episode in brief
You don’t have to do this alone. Entrepreneurship is lonely, and so is the executive suite. Few people around you understand what you’re carrying. Jon built this show so founders and executives can hear how others faced the same problems and what they did about them.
Entrepreneurs and executives are in the same boat. An entrepreneur sees a problem and takes the leap to solve it, usually with everything on the line. A senior executive faces many of the same problems while running a department or division. That makes the executive’s job, in effect, a business inside a business. The level of risk differs, but the work and the struggles look much the same.
Success means different things to different people. Jon traces his own interest in business to two films. In Pretty Woman, a buyer finds value in a struggling company by breaking it apart. In Wall Street, an investor looks for the next diamond in the rough. Both find value where others don’t. Jon has also watched people succeed through timing, through relentless hard work and, occasionally, through politics. Whatever got someone there, the higher they climb, the clearer it becomes whether they can lead, manage and deliver results.
There are ten traits, and Jon adds an eleventh. A July 2020 Harvard Business School article lists ten traits common to successful entrepreneurs: curiosity, structured experimentation, adaptability, decisiveness, team building, risk management, acceptance of failure, persistence, innovation and long-term focus. Jon adds one more: be a voracious learner. Whatever you haven’t experienced firsthand, you can learn from people who have.
Risk works both ways. Entrepreneurship requires taking risk, but it also requires keeping risk small. If you can’t measure and manage risk, the stress can wear down your health. An unmeasured bet on a hire, a campaign or a new market can also wear down the business.
Fail fast, fail often, fail upward. Dwelling on a failure keeps you stuck in it. Find the lesson, adjust and move on. You may repeat a version of the same mistake, but as long as you keep moving upward, you’re making progress.
In the end, mentality decides. Jon cites Dr. Carol Dweck’s research on growth mindset: praise effort, strategy, persistence and resilience, not natural talent. Traits can be learned, but mentality has to come from within. Too many aspiring entrepreneurs and executives focus on the skills and too little on the discipline needed to use them. Jon’s conclusion: real success starts with mentality and grows with the right traits.
Key action items
- Score yourself against the ten traits. Note which ones come naturally and which you’ll need to build or hire for.
- Run one structured experiment. Pick a single assumption about your business, test two or three approaches, and keep whichever one the evidence supports.
- Write down your last failure and its lesson. Then name one thing you’ll do differently next time.
- Make learning a habit. Set aside regular time to learn from people who have already done what you’re trying to do.
Listen next: Episode 2: The Origin of the Entrepreneur
Value Creation Consultancy™ has since merged into Founder’s Accounting™. References in this episode to the consultancy reflect the firm at the time of recording.
This episode is educational and isn’t legal, tax or financial advice. Speak with your own attorney and advisers about your situation.