I recently went one on one with Jukin Media co-founder Josh Entman. Josh is also the founder and CEO of Vinohead, a new media platform for the next generation of wine drinkers.

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?

Josh:  Thanks Adam. My journey here has been a fairly consistent path in digital media since its inception, first on the web 2.0 advertising sales side, then into online video with an expanded business development role, and finally into an overarching lead creative position. 

The biggest challenge has always been overcoming the underdog label. I’d be lying if I said it didn’t get old, but the truth is, so many of the failures and setbacks were predicated on being too early, too new, and perhaps too bold. But if you ask any founder, I think that’s the result of being passionate and prideful. You’re carrying out a vision that may not exist today. Hearing no and being misunderstood is par for the course. Not all people are that imaginative.

I’ve been part of several media startups at various stages since I began my career. The energy is unmatched. And I’ve always had my eye on the prize, whatever that was. Plenty of businesses were bigger, stronger, sturdier. But not faster, and never more determined. That’s the nimbleness and velocity that comes with being a startup, and ultimately, from being underestimated. That drive is potent. It’s not about proving people wrong as much as it’s about proving your supporters right. 

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

Josh:  I typically approach ideas like a songwriter. Sometimes you start with the music or the melody, sometimes you have the full lyrics written, and sometimes you just have the name of the song. There’s no prescriptive order. 

A business idea could simply be one note or one riff. But as you begin to workshop it and bring in additional artists, producers, and instruments, suddenly it evolves into a layered wall of sound.

My advice is to take an idea, any idea, and develop it into oblivion. Turn it into a full on orchestra. That’s the best part of being a dreamer. Bring out that absurdist mentality. The ability to ‘go there’ is important, not because that’s THE business, but because you’re experimenting without boundaries and being a creative thinker in the process. It’ll serve you better down the road as you face new challenges.

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

Josh:  First, I see something that triggers me. Whether it’s a statistic, a trend, a behavior, etc. Any strong signal or piece of validation to support my thesis. It gets my mind whirling. And last, I understand (and accept) the harsh reality that failure is a possibility. That’s an important piece to grasp. It’s not about self-doubt as much as it’s about pragmatism. You must ask yourself the question… Is it worth being wrong? For any ideas I’ve pursued, my answer has always been yes.

I’m very diligent in the discovery phase of exploring a new business idea. I spend countless hours doing research, whiteboarding, writing outlines, pitching ideas, and seeking advice from close friends and colleagues. But, inevitability is the one switch I can’t turn off. You start living with the notion that this ‘thing’ is going to happen with or without you. The universe has accepted it. If not you, someone else will do it. And that’s agonizing. So you either sit on the sidelines and watch someone else do it, or go all-in and start grinding. 

From there, I’m locked in. Build a product, test and iterate, and take away some learnings. Worst case scenario, you have to pivot and reevaluate. But that’s always better than waiting. 

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

Josh:  Stay focused. It’s easy to get distracted. You can always experiment in hopes of finding a sticky surface. But stay true to your core. it shouldn’t be a land grab. Do everything with intent. 

Trust your gut. Sometimes you follow the breadcrumbs and other times you go against the grain. But you have to rely on instincts, experience, and a few ounces of wisdom to stay ahead of the curve.

Invest in people. When you’re trying to reach new heights, hiring well and empowering your team is the greatest asset. It’s a pivotal stage. As a leader, your job is to guide a unified vision by making lives easier. Leadership must be shared. You can always be a player-coach, but trust is what lets the vision actualize itself. 

Adam: What are your best sales and marketing tips?

Josh:  Marketing tip… Be brand obsessed and know your audience. The greatest marketers find their way into our collective consciousness. It may be as simple as a clever tagline on a blank billboard. You’re not selling a one-time product, you’re selling a lifetime brand. This is true for a pair of sneakers as much as it’s true for a new car or cell phone. There are always new releases, new models, new features. Instead of one-off campaign-based initiatives, be laser focused on the adoption of your brand in its entirety. That staying power is unmatched. The product is simply a manifestation of that ideology. Your audience knows that.

Sales tip… Target the opposition. Study them. Like a great athlete watching game film and preparing for a matchup. In every room there will be people that agree and disagree with you. In sales, you’re always just trying to receive a majority of the vote in your direction. That’s the sway. But keep an eye on the naysayers. Listen to their feedback. It doesn’t matter if you agree with their assessment. Chances are you won’t. What matters is if you can learn to win them over. 

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?

Josh:  An effective leader is balanced between unflappable and elastic. Which is to say, there's toughness and durability with everything they encounter. They can bend and stretch and be nimble and pliable. Maybe even get a little beat up in the process—metaphorically. But their spirit never breaks. 

Nowadays, it’s okay to show vulnerability. You can be strong emotionally and still feel the effects. We don’t have all of the answers. But if you're a good listener and problem-solver, you will find a unique path to progress for each team member. Your truest leadership skill is being able to navigate all of the chaos while still executing a sound vision.

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

Josh:  Hire hungry. I love people who crave knowledge and want to be part of something bigger. They’re not just filling holes. They’re creating new opportunities that you never knew existed. Doers are the most underrated people in every organization. They’ll dig in, cut their teeth, do the work, and come back with results. 

Lead by example. Recognize talent and allow them to speak up, take ownership, and offset your weaknesses. Their unique perspectives help anchor different parts of the organization.

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

Josh:

1. Take the meeting — You never know what you may learn and listening is an essential tool.

2. Don’t believe your own hype — It makes you narrow, insecure, narcissistic, and pathologic.

3. Be uncomfortable  — It forces action, grit, and self-awareness.

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

Josh:  Don’t take credit. Take responsibility.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

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