7 Lessons I’ve Learned from Successful Entrepreneurs

The Begin Anyway Series was born from the idea that nothing is set in stone—it’s never too late to take a leap in the pursuit of success and happiness. If you are unhappy in your day-to-day trajectory, if something isn’t working anymore, if frustration and lack of fulfillment become the routine, you are responsible for creating an opportunity for change.

I have met and spoken with some truly inspirational individuals through the Begin Anyway Series. These people come from diverse backgrounds and operate in a range of professional environments. Despite this diversity of pursuits, I noticed that there were many commonalities—motivating words, reassuring advice, grounding daily practices—that are foundational for those we have featured.

Here are a few things that motivated the friends we featured on the Begin Anyway blog. I will continue to focus on these words of wisdom as my own journey continues into a new year:


1. Embrace Failure. 

Katy Lynch of Codeverse.

Failure is always an option – and sometimes the best option. Some of our greatest lessons are learned from moments of failure. What matters is how you react and recover afterwards. As Katy Lynch said in her interview, Simply put, as adults, we’re terrified of failing. And, the fear of failure stifles growth and creativity. In my opinion, we need to embrace failure. When you start a business, you fail constantly. Entrepreneurship is a rollercoaster. It’s scary, but it’s also incredibly rewarding – especially if you have the right attitude. Making mistakes is OK. The important takeaway from making mistakes is learning from them, picking yourself up, and quickly moving on.”

2. Never Stop Learning.

Nearly everyone we spoke with emphasized the importance of continuing to educate yourself – whether through reading, attending lectures, listening to podcasts, or observing the operations of your professional peers. NEVER STOP LEARNING. There are always opportunities to learn something new. As  Josh Kercher said, “I’ve always found ways to learn from the people in my life, good and bad. I’ve seen the effects of not believing in yourself or not going after something you’ve wanted and told myself that I would never fall victim to that.

Josh also finds that putting himself in situations where he is forced to learn can contribute to personal growth, and the realization of potential: “Stay as uncomfortable as possible. All of my biggest advances in life were directly on the other side of an uncomfortable action. Unwavering belief combined with massive action is a tried and true recipe.”

3. Fake It ‘Til You Make It. 

Sam Berngard of Boldface Co.

Let’s be clear. No one knows what the hell they’re doing. It takes passion, intelligence, and straight-up hard work to figure it out. Sam Berngard owns this mindset – we are all in the same boat. “I really act like an expert in everything when sometimes I have no clue what I am talking about. But the truth is that confidence and drive will allow you to accomplish anything you set your mind to!”

4. Just DO—Own Your Path and Own Your Success.

Your success is just that: it’s yours. No one else can get you there if you aren’t willing to take the hard steps yourself. And sometimes, you just need to START (fake it til you make it). As Alex Blair told me: The greatest things in life are created by doers, not dreamers. I’m constantly asked how I have accomplished all that I have while still in my twenties. My response is that I stopped asking people how they did it, and I did it for myself. I had zero experience starting a business from scratch. I launched fast, failed fast, and iterated as fast as possible to keep the lights on. Zero people are going to get you where you want to go. If you don’t get your butt out of bed every day — an hour before everyone else — you’re damn sure they are going to be one step ahead of you at every curve.”

5. Taking a Leap Doesn’t Necessarily Mean Jumping Without a Net. 

Arturo Gomez of Big Game Air.

Even someone going on a great adventure through the Amazon packs supplies, studies a map, learns about the people and animals, and prepares as much as possible for the unexpected. Leaping into entrepreneurship is no different. You are journeying into the unknown, yes; but that doesn’t mean that you should enter unprepared. It is important to cultivate a professional network, an understanding of the industry, and initial capital investments in advance of taking the leap.  

Arturo Gomez, makes a great point:  “Don’t be afraid to jump, but don’t ‘jump just to jump.’ Making big life changes requires a lot of thought and preparation.

Of course, it’s also important not to become too concerned with finding ‘the perfect time’ to begin. D. C. Crenshaw says, “There is no perfect time to take a leap of faith (unless you have a bunch of capital behind you.) I always tell people that if you’re not happy with your current situation, then find a way to make your dream situation happen. It doesn’t mean that you need to quit your job tomorrow, but have a plan that will allow you to eventually exit and work on your passion.”

6. Create Meaningful and Impactful Connections.

Treat those in your network – and everyone you meet – with respect and be generous with your intentions. As someone whose career has always involved building personal and professional connections, Jessica Zweig knows a thing or two about making a meaningful impact. We discussed how important this is in our conversation: When you’re doing networking right, it’s all about bringing value to other people and asking for nothing in return. Literally. Networking is about opening doors, making introductions for people and paying it forward. That’s how you create the strongest relationships – because people never forget. That kind of professional generosity creates a boomerang effect beyond what you might be able to see today.”

Building a network of people who inspire, motivate, and challenge you can pay tremendous dividends. This is also an opportunity to surround yourself with individuals who share your professional values. Arturo Gomez spoke with us about the importance of mentors and professional relationships. “The things that I have learned from them and that have helped shape who I am today are: hard work; humility; attention to detail; to always chase your dreams and your passions; and, most importantly, to be there when I someone needs guidance the most.

Jason Loebig of Live Better Co.

7. Maintain a Positive Attitude.

Remember: all storms will eventually pass. Many of those we spoke with emphasized the importance of accepting that shitty things are bound to happen. We will all have a bad day and we will all have those periods when we feel like everything is moments away from coming crashing down. Embrace these moments, give them their time, and then pick yourself up, with determination to move forward.

The importance of positive energy is best represented by my friend Jason Loebig. His motto, after all, is: ‘have the best day ever, every single day.’ “I have a set morning routine I follow to prime my day, and that includes cutting out the bullshit. I don’t check my email first thing, or my social media. I don’t read the news or watch morning TV. I read something, meditate, or just take a minute to stretch. A couple breaths, just for you, will mean the world of difference. There are so many inputs we receive during the day that cloud our energy for making decisions that matter, so why add the nonsense before your day even starts?”

Much love and gratitude to everyone who has contributed to the Begin Anyway Series. Cheers to an outstanding 2018!

Leave a Reply

Your email address will not be published. Required fields are marked *