A Decade in Review: 10 Lessons Every Entrepreneur Needs to Know

In 2010 I was finishing up my degree at Missouri; ready to fulfill my goal of becoming a sports agent/journalist. A worthy goal quickly derailed after realizing my true passion - building and scaling tech-focused businesses. This passion had been brewing since my early years learning ‘on the fly’ as my family’s distribution business grew from $30M to $500M. It grew stronger as I adopted these best practices to drive 3x growth as a District Manager for a Fortune 500 retailer.  

Since then, I have worn many hats in the startup ecosystem: consultant, angel investor, CXO executive, venture capitalist, operator, mentor, coach – you name it! At the end of the day, each of these roles connected back to a common theme… entrepreneurial mindset meets servant leadership.

And so, in reflection of my past decade as an entrepreneur and business leader, it seems as fitting a time as any to compile...

My top 10 startup lessons I learned the hard way so that hopefully you won’t need to:

Be Patient and Prepare for 3-5 Years of Hard Work:

This is what people tend to not talk about. It will undoubtedly take you 3 to 5 years of HARD work to start seeing some signs of success. You will have to develop a sense of building the right team, talking and listening to your customers, analyzing the market, nailing your sales process, networking, pitching your idea, and most importantly - learning from your mistakes.

Be the Leader that Everyone Wants to Become Rather Than the One Everyone Fears

Leaders are not meant to be praised, work the least, and take all the rewards. Leaders are to serve, support, and go the extra mile to make sure everyone gets what they want and contributes to the shared vision. Trust me, the people who work for you notice the little things, and it makes a world of difference.

You Can’t Teach Passion

The right team is a key success driver on your journey from startup to scale-up. A passionate team is more important than any idea generation or intellectual horsepower. Focus on creating the perfect environment to enjoy work and execute. Miscommunication, value conflicts, and general interest and buy-in can destroy your culture, and in turn, your growth stage company. Hire for passion, truly one of the only pieces within a company (product, tech skills, sales tactics, etc.) that cannot be taught. 

Partnerships are Hard, Align Expectations

When I started my first company I was 29; I did it alone - and learned a lot along the way. When I started my second company, I was 32, I did it with two co-founders - teaching me a lot of lessons in ‘partnerships’. Most of these lessons stem from the importance of ensuring all partners are aligned on expectations from day 1: responsibilities, tactics, roles, etc. Of course, things will evolve, after all, it is a startup, but having a baseline goes a long way in a successful partnership.

Equity is the Most Valuable Thing You Have. Only Give it to the Right People

What does every company start with? Two things: a passionate vision and a clean cap table. As you grow and expand, you will bring on a variety of partners - investors, growth partners, executives, employees, etc. - and in early to growth-stage companies, everyone wants a piece of the pie - as they should as it aligns long-term expectations. The problem lies in how equity is viewed in comparison to other forms of compensation. The more people value equity, the more passion they will likely show for the business. Make sure that equity compensation is aligned with the right people who are truly driving the business forward.

Listen to Your Customers and Nail Your ICP (Ideal Customer Profile)

So you have a few initial customers? That is no small feat, so congratulations. However, do not become complacent. Achieving product-market fit is not easy, and the early iterations of your customer will likely not be the same as your long-term ICP that brings you to scale. Think of the early adopter curve, you need those people, but most of your clients will fall into different segments, with different needs and desires. More on product-market specific to SaaS companies in my recent interview with Mitch Russo: 5 Lessons I Learned When I Created My First SaaS Company.

Avoid the Low-Cost Pricing Trap

Cost pricing dilutes value, especially for luxury brands. Focus on value-based pricing instead of being the ‘cheapest option’ in the market. It's better to have fewer customers who pay you big bucks rather than having thousands of customers who pay you pennies. Startups especially tend to fall into the low-cost pricing trap, which can haunt them for years to come.

Be a Lifelong Learner

The day I stop reading books will be the day I die. I may not plan on working my entire life (or certainly not to the extreme that I am currently), but I will never stop learning. This goes hand in hand with ‘hiring for passion.’ Lifelong learners are those who are driven to be them best selves and likely want to share that with those around them. The mantra, “You’re the average of the 5 people you hang out the most with” rings true here. Surround yourself with fellow learners, and you will never have a day where you do not grow. 

Always Be Transparent

People oftentimes lament (or tout, depends on whom you ask) the way the working world has changed. To hone in on one thing that’s truly changed the world, it’s the transparency in which we live by each day. Businesses, and the people in those businesses, are no longer in the shadows and those that understand that (and the opportunities it provides) are the ones who will be successful as the world continues down this path. 

Don't Take Your Business Too Personally

Your business won't take care of you when you get sick or feel down, your friends and family, however, will. Should you spend 60+ hours a week on your business? Yes! But 60+ productive hours also requires you to focus on your health, family, and relationships. This one is more like a life lesson (“The Hero Syndrome”), but life is one of the most powerful business lessons.

Recapping the Top 10 Lessons Learned, so that you won't need to:

1) Be Patient and Prepare for 3-5 Years of Hard Work

2) Be the Leader that Everyone Wants to Become Rather Than the One Everyone Fears

3) You Can’t Teach Passion

4) Partnerships are Hard, Align Expectations

5) Equity is the Most Valuable Thing You Have. Only Give it to the Right People

6) Listen to Your Customers and Nail Your ICP (Ideal Customer Profile)

7) Avoid the Low-Cost Pricing Trap

8) Be a Lifelong Learner

9) Always Be Transparent

10) Don't Take Your Business Too Personally

I hope you enjoyed and can’t wait to see what the next decade holds for both of us!

ABOUT THE AUTHOR

Jim Barnish is Founder and Managing Partner of Orchid Black (OB), a boutique firm designed for Tech-Forward, Growth-Stage Companies seeking to grow smart and grow fast. Spanning 400+ years of combined experience and more than $35B in combined value creation, OB’s team of highly skilled operators have repeatedly driven success across all stages of business from growth to exit. Jim's 15+ years of experience as a strategic growth leader in global and integrated M&A, operations, sales, and marketing uniquely qualify him to lead Orchid Black’s team of executives. @jimbarnish @OrdBlk