Alyssa Hoffman Wants You to Be #Fearlyss

by Jerome Knyszewski
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Alyssa Hoffman, CEO of Fearlyss Entertainment

Alyssa Hoffman bet on herself and won. Many would consider a cushy job at a Fortune 500 company to be the final goal for one’s career, but Alyssa knew she was meant to do more. After spending years at the company, and receiving honors such as “Board Member of the Year” and “Educator of the Year,” she decided to leave everything behind.

It was after meeting the band Wayland at a rock concert that Alyssa Hoffman chose to take the plunge. Shortly after, she quit her job, sold her possessions, and became the band’s manager. She lived in the tour bus with them, while boosting their profile among rock and roll listeners.

Through her business expertise and experience, Alyssa Hoffman secured several big-time opportunities for her band. Wayland performed on cruises, as well as landed endorsements and sponsorships. Alyssa also introduced the band to Rock Against Trafficking, so that they may support a cause bigger than music.

Of course, Alyssa Hoffman didn’t stop there. She also expanded her music career by rising to three top reputable positions. Currently, she is the Public Relations Marketing and Social Media Director for New Ocean Media. New Ocean offers a full range of management services, catering to clients like Capital Records, Def Jam Recordings, and Warner Music Group.

Alyssa Hoffman is also the head of artist management and brand initiatives for PennyFly Entertainment. At PennyFly, Alyssa instituted a “for artists by artists” company that boosts the profile of independent artists through promotions campaigns designed for major-label artists. Finally, Alyssa also manages Wayland through her own music management company, Fearlyss Entertainment.

With three top-level positions under her belt, Alyssa Hoffman has become a force to be reckoned with in the industry. She has also proven that you can gamble on yourself and come out on top.

Check out more conversations with industry mavericks here. If you want more of Alyssa Hoffman, check out her YouTube channel here.

Jerome Knyszewski: What do you think makes your company stand out? Can you share a story?

Alyssa Hoffman: Fearlyss Entertainment is not a traditional company, and it’s definitely not a traditional music company. Being “fearlyss” is a business that is in service to the artist. Fearlyss Entertainment trusts itself, and therefore it’s able to trust the artists with their own art.

Being “fearlyss” isn’t about doing the most dangerous thing, or risking it all for clout. Being “fearlyss” is about embodiment, that’s why I used my name in the spelling. It’s embodying the zero point. The stillness. Neutrality. From that place of presence and clarity, I’m able to make the best decision for the artist and their music.

Everyone thought I was insane to travel full time with the band and not have an office. I worked out of a bunk for two and a half years, gained ten pounds, and couldn’t move my back from being hunched over. But being on the road I listened to every conversation, every complaint, every prayer, and every piece of gratitude. It allowed me the opportunity to see the music industry first hand from the artist’s perspective which is something no school or mentorship would have ever taught me. This knowledge is what makes us different.

Jerome Knyszewski: Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Alyssa Hoffman: To avoid burn out, be fearlyss. When you are “fired up” and emotionally charged, you’re going to burn out. That passion flame gets hot too fast, and it will eventually burn you. When you are fearlyss, which is to say when you are neutral, you are present, you are listening, actively, to what wants to be birthed through you or through your artist, and you are controlling your energy. You’re turning up the heat slowly and intentionally to where you’re paying attention to what’s in front of you in that moment, in each moment, and that way you won’t get burned.

Jerome Knyszewski: None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Alyssa Hoffman: My mother has been responsible for getting me everywhere in my life. She coached me through cosmetology school, through my career with Great Clips…she introduced me to the band and encouraged me to tour. I called her the night before I was quitting my job after a decade and asked her what to do if I’m making a mistake and she reminded me that a mistake is a mistake for a minute, but a regret is for a lifetime. She is my best friend.

Jerome Knyszewski: Ok thank you for all that. Now let’s shift to the main focus of this interview. The title of this series is “How to take your company from good to great”. Let’s start with defining our terms. How would you define a “good” company, what does that look like? How would you define a “great” company, what does that look like?

Alyssa Hoffman: A good company is a company that functions. It profits, it treats its employees well, and it’s able to hold its own.

A GREAT company serves. It serves itself. It serves its employees. It serves its customers. It is in service to the highest and best good of all in integrity at all times.

Jerome Knyszewski: In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

Alyssa Hoffman: The most underestimated part of running a company is always your relationship with yourself. So many leaders will do everything for their business and do nothing for themselves, not realizing that they are that business. Soon, the external reflects the internal and you’re wondering why you’re not growing, why you’re burned out, why you’re unfulfilled. Decrease your workload by 20% and increase your self care by 20% and watch the profits match that 20% and then some.

Jerome Knyszewski: As you know, “conversion” means to convert a visit into a sale. In your experience what are the best strategies a business should use to increase conversion rates?

Alyssa Hoffman: Instead of thinking about making “sales,” I like to think about offering value. When you think about what the most valuable thing you can offer somebody is, and you truly believe it and know it like your own name, the conversions will come naturally. Being cerebral isn’t what’s going to create conversions. Stories sell. Feelings sell. Connection sells. Connect and feel and share your story behind your why. It wins everytime.

Jerome Knyszewski: Of course, the main way to increase conversion rates is to create a trusted and beloved brand. Can you share a few ways that a business can earn a reputation as a trusted and beloved brand?

Alyssa Hoffman: To earn a reputation as a trusted and beloved brand requires being in your integrity. When you are true and authentic to your values, your mission, and vision, and you embody that experience, the authenticity is magnetic.

Jerome Knyszewski: Great customer service and great customer experience are essential to build a beloved brand and essential to be successful in general. In your experience what are a few of the most important things a business leader should know in order to create a Wow! Customer Experience?

Alyssa Hoffman: The golden rule in every language is treat others the way you want to be treated. When you think about your most incredible customer service experience, do that, and do it better. Customer experiences are not just customer experiences. It is actual time out of a real person’s life. It is an interaction, a moment in time, that cannot be duplicated or replaced. Life is sacred, and business is sacred. Pay attention to the details and make every interaction better than your last.

Jerome Knyszewski: What are your thoughts about how a company should be engaged on Social Media? For example, the advisory firm EisnerAmper conducted 6 yearly surveys of United States corporate boards, and directors reported that one of their most pressing concerns was reputational risk as a result of social media. Do you share this concern? We’d love to hear your thoughts about this.

Alyssa Hoffman: Social Media shouldn’t be a concern. We give too much power to it. We have all given in to a “groupthink” mentality and are “afraid” to be “cancelled.” We have replaced pop culture with “cancel culture” and it won’t stop until we stop giving it our power. Forgiveness, grace, and resilience are characteristics of companies that I want to align myself with- as an owner and a consumer. This is our social responsibility to trust ourselves and not fall into the “but what will they think” mentality. Authenticity and integrity will always be my go-to answers.

Jerome Knyszewski: What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Alyssa Hoffman: The biggest mistakes I’ve seen CEO’s and founders make is giving up on themselves. It is not going to be easy. It is not going to be fast. It is going to ask EVERYTHING of you in every moment. Making mistakes is part of it. You’re not even making mistakes- you’re making discoveries. You’re discovering what doesn’t work which brings you closer to what will work. TRUST yourself. This is your religion, your mantra, your saving grace. You are who you have been waiting for.

Jerome Knyszewski: How can our readers further follow you online?

Alyssa Hoffman: or

I am live on WaylandTV every week on YouTube at

Jerome Knyszewski: This was very inspiring. Thank you so much for the time you spent with this!

Alyssa Hoffman: Thank you so much for #lysstening.

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