Story & Lesson Highlights with Kris Chaney of San Francisco

We’re looking forward to introducing you to Kris Chaney. Check out our conversation below.

Kris, really appreciate you sharing your stories and insights with us. The world would have so much more understanding and empathy if we all were a bit more open about our stories and how they have helped shaped our journey and worldview. Let’s jump in with a fun one: What is a normal day like for you right now?
A typical day for me starts with a morning workout to set the tone and focus for the day. From there, I juggle several roles as a business owner, account manager, producer, and journalist. During the day, I focus primarily on running my logistics business—managing operations, clients, and strategic initiatives. In the evenings, I shift gears into my role as a women’s basketball journalist for The Best Damn W Show, where I attend WNBA and NCAA games, cover press conferences, and create content. I often spend late nights recording or editing my next podcast episode, reviewing and refining content for Courtside REEL on TikTok, or catching up on games I may have missed while traveling for coverage. It’s a full schedule, but one that keeps me inspired and connected to everything I’m passionate about.

Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Kris Chaney, and I wear a few different hats — entrepreneur, producer, and women’s basketball journalist. I’m the founder of Kross Investment Holdings, a diversified holding company with ventures in real estate, logistics, and media, including KrossFleet, our mobility and transport division, Kross Inc. Apparel, an active & street wear clothing brand, and REEL Productions Network, a production company.

Beyond business, I’m the creator and voice behind Courtside Raised Podcast and Courtside REEL, platforms dedicated to amplifying women’s basketball through authentic storytelling and creative coverage. As a women’s basketball journalist, I cover the Golden State Valkyries of the WNBA and USC & ASU NCAA women’s basketball teams for The Best Damn W Show, where my goal is to give the women’s game the same energy, depth, and visibility it deserves.

What makes my story unique is how it all connects — from my military background to my years in corporate training and leadership development — every step taught me how to build, lead, and invest in both people and purpose. Right now, I’m focused on expanding KrossFleet’s national footprint while continuing to grow Courtside REEL into a full-fledged media outlet that empowers athletes and inspires fans.

At my core, I’m a builder — of businesses, brands, and better opportunities for others.

Great, so let’s dive into your journey a bit more. Who were you before the world told you who you had to be?
The world can never tell you who you are. Life will teach you what you need to survive its challenges but it can never tell you who you have to be. I think you grow as a person, when you finally are comfortable enough in your own skin and confident enough in your abilities to be able to tell the world who you are. It’s not about conforming it’s about growth and change and evolution.

I think as an entrepreneur, you learn how to stand your ground against conformity to achieve the things that help change the world. Back in my parents’ day, being an entrepreneur was like running away to join the circus — it wasn’t considered a “real job.” What people really meant was that it wasn’t a reliable source of income. But to me, entrepreneurship isn’t just something you do; it’s something you are.

As I explored my passions over the years, I realized I didn’t want to choose just one lane. That’s why it was always hard for me to pick a single career path — I’m driven by creativity, challenge, and curiosity in equal measure. I often use Flau’jae Johnson as an example — her dual passion for music and basketball proves that you can pour your energy into more than one calling and still find success in both.

What did suffering teach you that success never could?
How to be successful. You can’t be successful without suffering. I don’t mean that you cannot achieve success without suffering but in order to manage that success well when it happens, to continue it, and to grow it suffering is a stepping stone. You have to be able to rise from small tumbles in order to get back up after large falls. Suffering means hard times, it means challenges. The stronger you are, the harder your challenges are going to be. Suffering taught me to rely on God for all things because I can do nothing without Him. Keeping the faith in Him and continuing to move forward is how success is brought. Suffering is promised but so is eternal happiness.

Next, maybe we can discuss some of your foundational philosophies and views? Whom do you admire for their character, not their power?
Cheryl Miller. To add a little context for those who may not know who she is, she’s the greatest women’s basketball player to ever play the game. She once scored 105 points in a single game, sitting out the final two minutes of the game. Following her senior year at USC in 1987, she tore her ACL in a pickup game, and never played competitively again. Back to back collegiate national championships, an Olympic gold medalist, and at 22 years old, her playing career was over.

Most people would’ve walked away. Cheryl didn’t. A decade later, she became the first head coach of the Phoenix Mercury and broke barriers in broadcasting as the first woman to call a nationally televised men’s pro basketball game. Even today, she continues to pour into the game and the generations of women and girls who follow in her footsteps.

I think that’s what makes her story so powerful. To be as great as Michael Jordan — to have the game taken away from you — and still dedicate your life to it… that’s something deeper than talent. That’s love. That’s legacy. I’m sure there are moments when Cheryl misses playing, watching today’s athletes do things she helped make possible. But her impact is everywhere — whether they know it or not, they’re all playing in a world she helped build.

Okay, so before we go, let’s tackle one more area. What will you regret not doing? 
Great question. I would regret not doing anything I had a desire to do. Before I decided to do all I’m doing now, I tried to focus my entire self on one thing, every day. It was a horrible way for me to live because it reminded me of being in elementary school every day. Sitting in class staring out the window and imagining the endless world of possibilities going on out there. The only time I will stop “doing” is when my time on earth runs out. So I don’t plan on regretting not doing anything.

Contact Info:

Suggest a Story: BoldJourney is built on recommendations from the community; it’s how we uncover hidden gems,
so if you or someone you know deserves recognition please let us know here.
Highlighter Series
What do the first 90 minutes of your day look like?

Liz Hartman Sitaraman How we start our day is so important to set the tone-

Highlighter Series
What have been the defining wounds of your life—and how have you healed them?

Carey Selk A significant wound in my life I moved through was trusting my intuition.

Highlighter Series
Are you doing what you were born to do—or what you were told to do?

Culture, economic circumstances, family traditions, local customs and more can often influence us more than