My first foray into owning my own business was swiping snacks from the kitchen cabinet when I was a little kid and selling them to golfers nearby between their rounds. My margins were outstanding. That venture didn’t last long thanks to my parents discovering all our food missing, but it was a great lesson in vesting ownership and inventory management.
Here’s my point. Once you get a taste of entrepreneurship, it’s a tough habit to break. You begin to look for it all around and can’t help but ask, “How did this come about?” Of course asking about the mission behind a business is interesting, but what I find even more fascinating are the individuals behind successful companies and start-ups. Who are these men and women who spend countless hours away from family and friends and skip vacations for years on end to get their idea off the ground? Did they always want to be entrepreneurs? What sparked their business idea? What makes them tick? What do they wish they’d known to make the process easier?
As a person hungry for stories like these, I figured other like-minded individuals would be as well. And that’s why I started the Driven & Co. podcast. Today I talk to badass leaders from every industry you can imagine to explore their unconventional paths to leadership and how they arrived where they are today.
Some of the most interesting conversations of 2017 touched on how they overcame huge obstacles, navigated the detours, and learned to trust their journey. After all – let’s be real – entrepreneurship is no walk in the park. One common theme from all of the conversations this year was that as an entrepreneur, you’re never going it alone. You can learn from others and potentially avoid common mistakes along the way.
Here are a few of the best insights from 2017 Driven & Co. guests:
On seeking perfection:
“Don’t spend too much time in the proverbial basement creating what you think people want until you can actually talk to them with a product in hand.” – Nate Martin, Cofounder & CEO of PuzzleBreak
On women entrepreneurs overcoming challenges:
“I don’t think that there’s a glass ceiling per se in entrepreneurship. There’s more of a sticky floor. Women can think of every reason why we shouldn’t be entrepreneurs. Why the company would fail. Why someone else would be better at starting it then we would be. But I really feel like we’re at the tipping point for women’s entrepreneurship—there are suddenly enough women entrepreneurs that there’s room for people to mentor. Now women are exiting and investing in other women’s companies. That’s a very key point in the ecosystem.” – Danielle Tate, Founder & CEO of MissNowMrs
On what drives an entrepreneur:
“People get excited about a product or a technology. They don’t fall in love with a problem, and if you’re not absolutely 1000% in love with the problem that you’re trying to solve, it’s very likely you will fail. Because let’s be honest, starting a company is hard. It’s really, really hard. Anyone who tells you it’s easy is either one in one million or is lying to you.” – Inder Singh, Founder & CEO of Kinsa
On how to know if you’ve made it:
“There’s lots of different levels of making it, right? Creating a business that survives, solves problems and that people are paying for – that’s making it to some degree. Then scaling that business and hiring a bunch of people is another level. Then eventually exiting the business is another level and there’s 10 more levels in between.” – Steven Benson, CEO of Badger Maps
On asking for help:
“It’s a long game, so don’t think short term. I learned early on that no one knows everything and you’re never going to know everything. Being open to learning as you go and constantly improving yourself is a big part of being an entrepreneur, as well as constantly persevering through challenges and problems that you have.” – Andrew Chaiffetz, Founder & CEO of Notebowl
On constructing an entrepreneurial mindset:
“The thing that I got out of living in a house of entrepreneurs is I saw how hard my parents worked. They knew the harder and the smarter that they worked, the better the opportunity would be for them and the family. Now I’ve got three little kids and we talk about entrepreneurship. I teach them about the value of hard work. We introduce them to entrepreneurs. We talk about business and things like that. My kids are likely to be entrepreneurs, or at least, they’ll have an entrepreneurial mindset wherever they end up doing. Anybody can get this mindset. I don’t think it’s born with you.” – Joshua Dorkin, Founder & CEO of BiggerPockets
On preparing to scale:
“I think the one piece of advice would be getting a CEO coach. I found tremendously helpful. Find someone who’s done the journey before, who’s worked with other CEOs, who has a lot more knowledge and can help guide your thinking and provide advice and expertise.” – Raphael Crawford-Marks, Cofounder & CEO of Bonusly
Which was your favorite episode of Driven & Co.? Did any advice stand out or inspire you?
Meet Justin Gray
Justin is a serial entrepreneur and the CEO and founder of LeadMD, the world’s largest revenue operations agency having implemented over half of the Marketo user base. Justin has made a career of launching successful companies and scaling them, with successful exits of over 200MM+ in the last decade. Justin’s latest endeavor launched in 2016 when he co-founded Six Bricks an online learning startup designed to combat employee and customer churn through experience-based education. Over the past 10 years, Justin has emerged as a strong voice for entrepreneurship, marketing and culture. As a recognized speaker, Justin has been published over 350 times in industry publications and holds his own column, Tribal Knowledge in Inc., while writing for Entrepreneur, Tech Crunch and others. Justin and his wife Jennifer met over marketing and three years later welcomed their son, Grayson, into the world in April of 2017.