We were lucky to catch up with Jamie Hess recently and have shared our conversation below.

Hi Jamie, thanks for joining us today. One of the things we most admire about small businesses is their ability to diverge from the corporate/industry standard. Is there something that you or your brand do that differs from the industry standard? We’d love to hear about it as well as any stories you might have that illustrate how or why this difference matters.

I started my career in Public Relations, spending 17 years as a high level PR executive representing brands like McDonald’s, General Motors, W Hotels, LinkedIn, and more. When my own personal Instagram account took off (I call myself an “accidental influencer”), it quickly launched “Act Two” of my career as an influencer, and eventually I was able to leave my full-time agency job to be a full-time content creator.

Many people – including my own mother – thought I was crazy, and that it would never work out. Not only did it work out, but I 5xed my income within 18 months.

Here’s the reason why: right off the bat, I approached brand deals differently than 90% of influencers.

Coming from the PR world, I knew how to structure them in a way that was strategic and “sticky” (I have a whole system for curating opportunities for brands that is more 360 than your “typical influencer”), and also I approached the sales piece totally differently. I believe that pitching, landing deals, and being a good partner is an art, and it’s as much about mindset / intention as it is about tactical / practical.

I have continued this cadence of successful brand deal sales ever since (I left the corporate world six years ago), and have earned well into seven figures from brand deals in the time since.

Today, I call myself & the course I teach “Brand Ninja” because this is my special sauce. I often joke that there are many things I don’t do well in this life… I am a terrible cook, I can’t keep a houseplant alive to save my life… but at securing high paying brand deals and helping others do the same, I can not be beat.

So many people want to make money doing brand deals on social media, but most people get discouraged in trying to lift it off the ground. I believe that most people just need some guidance and a confidence boost, and success is way closer than they realize.
Lots of people ask me why do I bother teaching it – I already make so much money doing it, why bother helping others? The answer is simple: there is nothing I love more than seeing people win… and there is enough money for us all. The creator economy is a $250 billion category (*according to Goldman Sachs). There is no lack of opportunity here.

I love helping people crack the code on brand deals, and I’ve had countless brand marketers tell me that “no other influencer thinks or pitches like this!” which is music to my ears.

Jamie, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I started life in a bit of a unique position – my mom is TV journalist Joan Lunden. She found out she got the job as co-host of Good Morning America and then immediately following that news she learned she was pregnant with me. I quite literally grew up on the set of Good Morning America, and as such, I was inspired by her every day. I learned a ton about media, star power, and how the entertainment industry works, and it led me to my role in public relations.

That said, it also led me down a separate, darker path: as a young adult, I felt like I was living life in her shadow, and it became overwhelming. I escaped into a life with drugs & alcohol. I almost died.

In my twenties, I got sober, and this formative decision would shape the rest of my life. In getting sober, I learned a new way of operating. I learned discipline, integrity, being service-minded, spirituality, and most importantly, I learned the fundemental idea that “an attitude of gratitude is the heartbeat of happiness.”

I took that and used it as my north star. Once I left corporate life and began a career as a media personality and content creator, all of my focus was around helping people live their best, healthiest lives. Whether it was through fitness & health or through confidence and an abundance mentality, I was determined to help people see life through a lens of gratitude and possibility.

Today, this guides my business, both in what I teach and how I operate. I’m proud that when people take my coaching course, Brand Ninja, they are surprised to find it doesn’t feel like “just another course on how to be an influencer.” In fact, it’s quite the opposite.

It’s as much a course on how to operate happily and successfully in life as it is a toolkit for influencing. We ask the important questions “why do you want to hold influencer? What do you want to say? What do you hope to inspire people to do?” I believe that once you’ve answered those questions, you are much more likely to get those high paying brand deals… for a very important reason:

You have substance.

Many people look at paid content creators as shallow or vapid, and the look at the whole space as silly or pithy.

I say this: there are bad actors in any space, and that is certainly true in the world of content creators. But those of us who are consistently earning six and seven figures with bigger, weightier brand deals are not getting paid that type of money because we’re simply holding up a tube of toothpaste, waving our hands around, and saying “buy this toothpaste.”

People who make the most money doing brand deals have put a tremendous amount of effort and intention into nailing their own personal brand first.

What do I stand for? What do I believe in? How can I inspire others in the best way possible? What message do I want to put forward to the world?

I truly believe that when you are grateful for your influence, you use it properly. I also believe those of us who have been to the darkest places see the light that much brighter… because I almost died while going through a hard time. I wake up every day with gratitude in my heart, grateful to just open my eyes and take a breath and be here to experience another day. The fact that I get to share about brands I love on social media and prosper from that is icing on the cake.

When we are operating from this level, everything else starts to click into place… and when I teach Brand Ninja, my intention is for my students to come out on the other side an entirely new and improved version of themselves.

Can you talk to us about how your side-hustle turned into something more.

I worked in Public Relations from the time I was in college until six years ago… and the funny part was, I didn’t leave that career because I didn’t like it. Quite the contrary – I loved doing PR! I was really good at it too (if I may say so myself!). I had worked my way up the ladder and was the SVP of a big agency, specifically running the book of business on McDonald’s, which was my primary account at that time.

Ironically, I was also a fitness & wellness junkie. I loved working out and eating healthy, so everyone thought it was funny that I worked on McDonald’s… but I loved it. I’ve always said working on the McDonald’s account was like going to business school. I learned a ton, as we oversaw all of their celebrity / influencer and experiential marketing.

I also represented Barry’s Bootcamp, and one day while I was running on the treadmill there during my morning workout, my now-husband surprised me after the last sprint by getting down on one knee and proposing. That moment went a bit viral, and it launched our public-facing persona as a “fit couple” which spurred our growth on Instagram. My account was originally called @nycfitfam (today, my account is my name @jamiehess), and it grew steadily. As I started doing a few casual brand deals here and there, I immediately realized my organizational pedigree in coming from the world of corporate PR – where I was the one writing the influencer briefs on behalf of brands like McDonald’s – was going to help me greatly. I already “spoke brand.” I knew what was appealing and how I could best move the needle as an influencer.

Within less than a year, my “side hustle” was outpacing my full hustle, meaning I was making more monthly that I was making from my six-figure paying agency job.

When I left that job, I did it with extreme foresight and precaution. My husband and I looked at a few numbers in particular, and he gave me a challenge – he said: if you can match the monthly amount you make as the SVP of this agency, plus whatever else you’ll need to take on that is currently subsidized by your employer (i.e my family’s insurance, etc) for four months in a row, then you can give notice.

And that’s exactly what I did!

One other thing I’ll say is this – there was definitely a period of about six months where I was flailing a bit. My biggest problem is that I’m overly ambitious, so I took everything from my vision board and essentially tried to do it ALL at once. I realized I was going to ended someone to help me with deadlines and deliverables, so I hired my first business coach. I strongly believe that if you’re a soloprenuer and you don’t have a boss, you had better hire one!

Today, I act as this coach for many soloprenuers, helping them to give shape to their goals and helping them back into manageable timelines to prime them for success.

Has your business ever had a near-death moment? Would you mind sharing the story?

Any entreprenuer has had close calls where things come down to the wire or money is tight. I liked to joke in the beginning that it always felt like I weather had $200k in the bank or -$200… there was no in between!

That said, the reason I love doing brand deals so much is that it becomes a commodity that you always have to sell… in other words, if you sell hard goods, you may have manufacturing problems. If you import goods, there could be tariff issues or anything else that rears its head in this tenuous global economy… but a content creator can always create, and if you’d built a good following and make good content, you should always be able to sell yourself out of a picky.

One story I can share just happened to me last year, and I share the whole case study in my coaching course, Brand Ninja.

I had to go to the west coast for a few days of shooting for my podcast, but I was low on funds. I needed some working capital STAT… so I decided to sell my way out of it with a quick, creative program that I designed in a few hours.

I would put together an opportunity for a brand to buy-in to this podcast shoot, promising them on-set product placement amidst my high profile guests, several social posts from me, and some original, bespoke content that they could use on their own social channels.

I priced it smart, using a system I teach in Brand Ninja where I use value stacking and comparative positioning around the value proposition based on what I know about the marketplace (i.e what the client would pay a creative agency for this content, versus simply hiring me to do it at a much more advantageous rate).

By doing this, and being nimble enough to turn it around to pitch in one day, I was able to comfortably fund my trip – which, of course, gave me the ability to create more podcast episodes which I could then turn around and sell advertising against… so the flywheel continued spinning.

It’s why I like teaching entrepreneurs and thought leaders at all stages how to become paid content creators – because it’s a wonderful way to earn “side hustle money” that you can reinvest into the primary areas of your business that you wish to scale.

Contact Info:

• Website: https://meetjamiehess.com/
• Instagram: https://www.instagram.com/jamiehess/
• Facebook: https://www.facebook.com/profile.php?id=61561384172570
• Linkedin: https://www.linkedin.com/in/jamiekrauss/
• Youtube: https://www.youtube.com/@Gratitudeology
• Other: https://podcasts.apple.com/us/podcast/the-gratitudeology-podcast-with-jamie-hess/id1717429278