Business Tips From a Serial Entrepreneur

John Headshot Demo Day.jpg

I recently spoke to John Cascarano, founder of Tame the Beast. Before launching Beast Brands, John was a founding team member of Mental Floss while in college at Duke University, built the online beauty product retailer Lock & Mane, and served as E-Commerce Director for ABLE, a women’s apparel and accessories retailer with the social mission of ending generational poverty.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth?

John: In my life, I’ve been fortunate to be a part of three businesses as a founder or co-founder. Each started at a difficult time. One right after the dot-com bust, one right after the 2008 financial crisis, and one during my father’s ultimately fatal bout with brain cancer. Each nearly went bankrupt and reached the point where I didn’t know how they’d continue and how I’d feed my family. I’ve learned that there are opportunities in both good times and bad and that grinding through tough times leads to a stronger mindset.

Adam: How did you come up with your business idea? What advice do you have for others on how to come up with great ideas?

John: I am so fiercely independent, stubborn, and desiring recognition and achievement, that all I did was pick a not terrible idea, convinced myself it was an amazing idea, and pushed forward until it became something resembling a business. Then, nearly going bankrupt (each damn time), and incredibly afraid of failure, I carved out a way to make a living (for now). And I may still fail.

My advice is don’t do it the way I did. I’d suggest a more studied approach: find a market opportunity, create a plan to capture some of that market, raise money if needed, and be ready to adapt quickly.

Adam: How did you know your business idea was worth pursuing? What advice do you have on how to best test a business idea?

John: Convincing myself was easy. I said, “Yeah, I’d probably pay money for that.” Then I jumped in the pool. Convincing others is a lot harder.

The only real test is the in-real-life behavior of people in the marketplace. Can you acquire customers in a way that you can sell them something profitable? Can you get people to invest in your business who really know your sector? 

If you can, you’re in business!

Adam: What are the key steps you have taken to grow your business? What advice do you have for others on how to take their businesses to the next level?

John: I have a tendency to be a lone wolf. I was pushed out of a company because of it. Delegating is hard for me. Not overly competing with people on the same team is hard for me. I’ve grown in business and matured in life by being self-aware and working with people that complement both my strengths AND weaknesses, and learned to thank and respect people who tell me what I don’t want to hear.

Adam: What are your best sales and marketing tips?

John: Everyone is mostly doing the same thing, like spending lots of cash on online ads, because some other smarter-than-them entrepreneur made it easy to do so. But the house always wins and other people have more cash than you. Don’t be a sheep. Be a sneaky creative wolf at customer acquisition. 

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

John: Maybe it’s just the current state of things in the world right now, but the qualities that spring to mind are perseverance, persistence, and getting continuous buy-in from great people during good times and bad. Every single leader faces adversity (great book by Doris Kearns Goodwin, Leadership in Turbulent Times, on the topic). Great leaders find a way even in bad times “to channel their ambitions and summon their talents to enlarge the opportunities and lives of others.” 

For someone hyper competitive like me, this can be really difficult. However, I’ve learned strategies to uplift others (and the circular benefits that result). One is simply asking authentic questions to learn what is most important to them right now and then later doing something helpful for them.

Adam: What is your best advice on building, leading and managing teams?

John: Finding new, good people, is hard AF. Take it from a lone wolf. My best asset is the people who, for better and worse, got my back already. So I listen to them. Then, through existing people, more good people follow. 

It just makes sense--we all know someone awesome at something. My brother in law turned out to be this awesome operational thinker. Just a guy I ate turkey with at Thanksgiving for years before it clicked. 

Jay is a big stakeholder in the company now. I first met him on the set of our first shower commercial through our videographer, who is a mutual friend. Jay joined the company and later we pitched and managed to convince Kelley O’Hara, a USWNT player, to join the company. Boom. 

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?

John: 1 .Maintain long relationships.

2. Do things outside of work that you love to do.

3. Valar dohaeris.

Adam: What is the single best piece of advice you have ever received?

John: From my grandfather, a great doctor who just passed at 93: 

“Do something that makes you excited to wake up each morning.”

Adam: Is there anything else you would like to share?

John: I’ve never regretted spending time with my family and friends.

Adam Mendler