Blue Sky Riders on the Today Show: (from left) Hoda, Kathie Lee, Kenny Loggins, Georgia Middleman, Gary Burr

Never too old to Dream… or to Re-Brand

Skip K. Franklin
6 min readJan 5, 2016

I was having dinner with Kenny Loggins who had just started a new band after being told he was too old to start a new band. I don’t have a bucket list, but if I did, “dinner with Kenny Loggins” would probably be on it. I’d been following his career and loving his songs for decades, but on that night I got to see his entrepreneurial side. At the table were the two co-founders of Kenny’s new group Blue Sky Riders, Gary Burr and Georgia Middleman. Accompanying me was my Serial Entrepreneurs Anonymous co-founder Dave Jaworski. The Blue Sky Riders story is a great one. And we were fortunate to hear some of the additional details that evening:

Kenny Loggins & the origin of Blue Sky Riders

In 2008 Kenny had been writing songs with hit songwriter Gary Burr in Nashville. Gary is an award-winning songwriter with many #1 hits and has a great sense of humor; a wise choice. But Loggins recalled what really struck him about Gary was how well their voices blended. It reminded him of his early days as Loggins & Messina.

Some time later Kenny approached Gary about forming a band. Gary had spent three years as the lead singer for Pure Prairie League earlier in his career and was open to the concept. When Kenny suggested they bring in a female vocalist as well, Gary recommended Georgia Middleman, a popular singer-songwriter in Music City. Their three-part harmony was magic, and they started writing songs in Nashville to fit that magic. The genesis of BLUE SKY RIDERS had begun. Now here comes the entrepreneurial part.

Trusting the Experts vs. Trusting your Gut

Kenny Loggins, when exploring the thought of starting a new group, wisely took counsel from trusted friends and advisers. Some very experienced and trusted sources advised Kenny NOT to do it. Their reasons were sound I’m sure. I wasn’t there, but here are some sound reasons I can come up with:

  • Your Cash Cow is your best ROI. Focus on your playing your hits. You can play your hits at festivals in front of huge crowds as you ride off into the sunset. You have a good cash machine going. Don’t mess with success.
  • New bands take time and effort. It’s tough to build a new brand. It’s a risky proposition. And it takes your focus and resources and effort away from your current activities. (You’ll be losing money for all of us!)
  • A new brand might confuse your fans! This argument has some merit. Certainly John Mayer “solo” opening for John Mayer Trio followed by the John Mayer band in the same evening was rather confusing. But Miranda Lambert has her Pistol Annies. Jack White has his White Stripes, Dead Weather, The Raconteurs, etc. In an age of websites and links, it’s not that hard to position additional brands and link them all together into a branding architecture that makes sense.

In any event, Kenny Loggins’ instincts were saying “Yes.” Artistically it seemed like a great project. It was making things fun for him again. He could have his new band, Blue Sky Riders, open for his Kenny Loggins Band. It was worth a try. As he was leaning toward following his gut, one of his close advisors pushed him over the edge with these final words, “Plus, Kenny, you’re too old to start a new band.” That did it!

The Entrepreneurial Spirit

Not only did those words “you’re too old” push Kenny over the top, he did what every songwriter should do, he used it as fuel to write a new song. “DREAM,” by Blue Sky Riders, ends with the words, “the day I ever get too old to dream.” I love this song. My entrepreneurial anthem. It starts out:

DREAM by Blue Sky Riderswho are you to tell me what I can’t do
well, that ain’t right
as if all I’ve been’s all I’m ever gonna be
for the rest of my life
you take the glory days
I’ll take what’s on its way
all I can do is believe in myself...
(Kenny Loggins, Georgia Middleman & Gary Burr)

Where Business Logic Fails

Let’s face it, no one saw Amazon coming, or Google or Facebook. There were lots of sound “business logic” reasons why they would never be big winners. But there’s something about momentum and buzz. There’s something about being a pioneer; about having a great story. I don’t think I’ve ever seen a company get as much free exposure as Amazon. It was the poster child of ecommerce. All three companies have had great stories. And that led to a lot of media exposure long before they were huge successes.

In Kenny Loggins’ case, the experts didn’t foresee the huge windfall the new band would get: media coverage. Kenny lamented to us over dinner that he had poured a lot into his last two solo CD projects and they had generated very little response. Few quality reviews and articles. Hardly any television talk show performances. And then comes BLUE SKY RIDERS. A fresh brand. A great story. An entrepreneurial risk. A new start-up. What followed? Lots of interviews, articles and television appearances. Blue Sky Riders had made Kenny “newsworthy” again.

Continual Re-Branding

Kenny’s story inspired me to do some re-branding for 2016. I’ve connected with a sharp firm in San Diego. I realized that no matter what you’ve accomplished in the past, it constantly has to be communicated in the context of today. You don’t have to reinvent yourself necessarily, but it might be worth consideration. As accomplishments fade and victories become old news, you have to work on developing your new story. And that often requires some re-branding.

I was invited to a movie set in London a few years back. The director was amazing, and he happened to be the director of one of my favorite Irish films. I asked him what that success and OSCAR exposure meant to his career. He said the immediate impact was insane. But that five years later it was right back to “So What Have You Done Lately?” I think many of us serial entrepreneurs can relate to that one.

It seems like the marketplace shifts every five years. And so I’m thinking that perhaps every five years I should be looking at my own development and re-branding to stay current and newsworthy. And this is hard to do in a vacuum. You really need outside forces to help forge the new path.

Entrepreneurial Stories Wanted

At Serial Entrepreneurs Anonymous we are looking for serial entrepreneurs with stories about re-branding. Company re-branding is often part of a strategic “pivot” or “right turn” by the start-up. When marketplace or situational factors, or a huge, unforeseen opportunity, force you off-plan. Serial entrepreneurs often have a better chance of justifying pivots and re-branding to key investors and board members. Whereas a newer entrepreneur often will follow the original Plan into the abyss. I already have too many stories of that scenario.

Backstage with Kenny Loggins

Dave and I enjoyed being backstage to see Blue Sky Riders sing their harmonies, followed by Kenny Loggins’ band playing hit after hit after hit. What a career he’s had, and as you now know, it’s far from over. We were privileged to be at their very first performance of Blue Sky Riders in 2011 at Tin Pan South festival in Nashville. It was an historic event. And great to see how far they’ve gone since then!

For you Kenny fans, I can say he is every bit as witty, energetic and playful as you’d hope he would be. He defies his years and keeps us all young in the process. Has it all been “red carpet” and “perfect life” for him. Research it a bit and you will see he’s had the same personal challenges and financial challenges that we all go through. Mountaintops and valleys. And here is today, eyes sparkling and having fun doing what he loves. A true winner. A great American success and re-success story.

And now we can admire him as an entrepreneur. When these legacy artists finally get on their own, they often start off with very little metadata from the millions that bought their albums and the millions that attended their concerts. Except for their great talent and famous brands, they are often starting from scratch to build up their businesses — from fan databases to newsletters to online merchandise stores. They have to become entrepreneurs whether they want to or not.

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Skip K. Franklin

serial entrepreneur, producer, author, zone ranger, digital media sherpa, technology exec & online community pioneer