9 Lessons to Learn From Being in the Entrepreneurial Trenches


Once upon a time, my wife Jenna and I and our three kids under ten moved from San Francisco to Los Angeles, had another baby, and bought our first house together. This, we thought, is the perfect time to quit our jobs and start a business! [eyeroll]

The idea of our company, Be Courageous, was born during the facilitation of a client session when the team was at odds with each other while exploring the future of their business. This quote from George Prince was on the wall: “Another word for creativity is courage.”

I realized many of us stay trapped in old thinking and actions when we lack the conditions to be creative and courageous.

A question emerged for me, “What would a world with an abundance of courage look like? How can I help create it?”

With my experience in marketing, strategy and facilitation, and Jenna’s in psychology, human resources and operations, we founded our business consultancy, Be Courageous. Every year we’ve grown. Every year our impact has expanded. Every year we’ve learned.

9 lessons from five years of learning

As any reader here knows, starting and running a business is a piece of cake. Ha!

For real, here is what we learned, having grown our U.S. business of two to a worldwide organization with dozens of clients and 35+ network partners while positively impacting nearly 1 million people in 82 countries.

1. Agility

One of our most in-demand programs with Fortune 500 companies this year has been our training on agile leadership. When you own your own business — the unexpected will happen. A successful entrepreneur adapts to new challenges and situations and creates lemonade from lemons.

We have created programs we never thought we would in response to what the world has needed from us.

Have a solid plan, but be flexible.

2. Purpose

We aim to activate courage in companies worldwide and align them with a planet-beneficial future. Yours might be to improve humanity’s mental health or lessen people’s stress by building an easier-to-use product. Whatever your purpose is, make sure you’re deeply passionate about it and that it fuels your actions.

Use the strength of your purpose to courage through challenges.

3. Superpowers (and kryptonite)

We found more success when we identified and focused on our greatest strengths. We aligned our strengths with our values and the services we wanted to provide to our clients to solve a problem they faced.

For example, my superpower is guiding businesses to realize their potential and future. My kryptonite is getting tripped up in the micro-details of spreadsheets. That’s where Jenna comes in. She leads operations with her superpower of keeping our company financially stable, growing and on the ground. I’m the visionary, and she makes it possible.

Align your superpowers with your business goals and values. Find people who have superpowers you lack.

4. Curiosity

In an exponentially-changing world, having an open mind is the key to running a successful business. Be curious about skills you don’t have and new ways to solve problems. Challenges will arise, but if your curiosity remains peaked, you’ll always get to the solution positively. Ask, “What is the courage needed in this situation?”

Curiosity may have killed the cat, but it feeds company growth. (We’re a dog company, anyway, no offense to cats.)

5. Healthy company culture

Create a team that feels safe, strong, empowered and able to share and receive ideas. When you foster personal connections with your team and your clients (yes, business is personal), you will thrive beyond competitors who are only in it for the buck.

Develop a positive company culture to unlock the full potential of your team.

6. Operational foundation

While you don’t want to get bogged down in systems and processes, your business won’t thrive without a solid operational foundation. Get an understanding of legal, financial and team infrastructure.

Stay pragmatic and, as we like to say, “aggressively conservative.” We make leaps, but only with a net.

Develop systems to streamline your business, so you can focus on serving your customers.

7. Integrity

Many people make empty promises, which erodes trust over time. It’s far better to over-deliver on your word. Pay what you say you will, earlier than you say you will. We’ve established deep, trusting relationships with our clients. We foster community.

We get callbacks five years after doing one program with a client because we don’t burn bridges; we build them.

Show up with your heart, don’t be a jerk, and honor your word.

8. Optimism

Never doubt what you can achieve, yet don’t be disillusioned. Approach everyone you can as a holistic human being, putting aside bias. Presume positive intent and look for positive solutions. Expect people to be their best until proven otherwise. And even then, be graceful about terminating any relationships.

Work and live from a place of abundance, not scarcity.

9. Mindful hiring

Be thoughtful about who you bring into your organization.

We hire a type of person — not only for the exact level of expertise we need. We hire people in love with our vision. A person who can be adaptive and learn with us. Who is willing to put in the work for a shared purpose.

Hire the right puzzle piece for your vision, not just how they look on paper.

Bottom line

Owning your own business isn’t for the faint of heart. It’s an ebb and flow of successes and learnings. But 20 years from now, if you look back, would you regret not doing something about your big and burning idea?

Fear will never go away, but when the desire to fulfill your purpose outweighs the fear of risks involved, that’s when you know you’re made to be an entrepreneur.

ENTREPRENUER