How do you handle 14,000 new customers a day? You act like failure is just around the corner and keep pushing.

That was my biggest takeaway from day two of Inc. 5000 in San Antonio. Mailchimp co-founder and CEO Ben Chestnut blew my mind when he shared that even at $600 million in annual revenue, he still feels like he hasn't made it and works every day to keep climbing.

Interestingly enough, I also heard that from a hundred women this morning over bacon (my superfood) and coffee at the Chase for Business "The Women of Inc. 5000 Breakfast." These high-growth female founders channeled Brené Brown in embracing their vulnerability to share that they still feel imposter syndrome. Despite their success and achievements, they still feel that being a woman leader in a male-dominated world makes them work insanely hard every day even when they pass their male counterparts in revenue.

The running themes today were around personal leadership, the resiliency required by entrepreneurship, and the drive to be courageous. These are the top four lessons I learned on day two.

1. Embrace the suck.

Brené Brown taught us that to be a truly courageous leader, you have to identify the factors keeping you from positive change, and many of them, in her words, just plain suck. Some of the top barriers she identified were tough conversations, fears, shame, lack of inclusiveness, and, yes, perfectionism, but good leaders face those blocks with courage and honesty.

2. Be a rational optimist.

Or, in other words, be the person your dog thinks you are. Bert Jacobs, co-founder of Life Is Good, emphasized that there is profit in optimism and doing good, a philosophy that had the crowd amped up. He also reminded us that entrepreneurs are perhaps the most impactful group in the entire world. 

3. Manage all members of your team, even the "always say yes" employees. 

In a review of her Four Tendencies personalities paradigm, Gretchen Rubin talked about the importance of recognizing our own strengths and weaknesses, as well as those of our teams. One tidbit particularly struck me: Even overperformers--the ones that always say yes--need your leadership to ensure they don't burn out. These employees often take on more than they can handle in an effort to please, which makes them the most prone to burnout.

4. Build your own personal board of directors.

My second biggest takeaway today was that the best advice might not be onstage but to your left and right. Some of the greatest advice and mentorship can come from your peers who are sitting right next to you. There is so much we can learn from one another, and it's also vital that we pass on the lessons we've learned to other entrepreneurs--from those with just a spark of an idea to those with multibillion-dollar companies.

Every single business owner in the history of time knows that this gig is hard. We also know that we can't go it alone; each and every one of us has achieved success with supporters, advocates, and teams by our sides.

Inc. 5000's most popular section today was called Sessions in the Round, a mentoring track with small groups convening around topics like venture capital, marketing, storytelling, and strategic growth. I saw the power of peer support happening in real time (with a line to get in, the need was clear). That means you have the best advice and the person next to you might be your best listener.

What's Ahead

Today is another jam-packed party to stretch and challenge our minds and businesses. In the morning, I'm especially looking forward to hearing about conscious finance from Ron Shaich, founder and chairman of Panera Bread, and designing a billion-dollar business from Kendra Scott. In the afternoon, Sessions in the Round with Alice will return with 11 more table leaders. So, let's be courageous. It might take a few beers, but you can do it.

Cheers, y'all!

Published on: Oct 19, 2018
The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.