Advertise on podcast: Kenversations with Ken Okonek

You don’t have to build the biggest business. You have to build the right one. Kyle has spent nearly 30 years proving that. He built a career around fishing, adventure, travel, and some of the most remote places on the planet. He moved to Alaska without much of a plan, built his reputation as a guide and operator, traveled throughout Patagonia selling experiences he knew firsthand, started over more than once, and eventually found his way to leading Aleutian Adventures. And he did it without giving up the reason he chose this path in the first place. In this episode of Kenversations, Ken Okonek and Kyle Kolodziejski get into what it actually looks like to build a business around what you value. They talk about betting on yourself, taking calculated risks, hiring for character over credentials, controlling the things you can control, earning customer trust, and recognizing that more growth isn’t always better growth. That last one is a big part of how Kyle runs Aleutian Adventures today. They already have demand. They already have waitlists. They could market harder and reach more people. They intentionally choose not to. Instead, the focus is on attracting the right people, protecting the experience, respecting the land and fisheries, and making sure growth doesn’t destroy the exact thing people are coming to experience. Kyle also shares why some of the hardest moments in his life led to his biggest pivots, how being stranded in Argentina during COVID changed his path, and why he believes following passion instead of money has ultimately created a pretty rich life. And as AI and technology take up more of our lives, Ken and Kyle get into something that may become even more valuable: Places where you can actually get away from all of it. This one is about business, but it’s also about having the guts to build a life that actually looks like yours. Subscribe to Kenversations for more conversations with entrepreneurs, leaders, and people willing to do things differently. In This Episode: Kyle and Ken dig into building a career around adventure, taking calculated risks, hiring for character instead of technical skills, the business behind world-class outdoor experiences, building trust with customers, responsible marketing, intentional growth, protecting Alaska's wilderness, and why unplugged experiences could become even more valuable in an increasingly digital world. Chapters: 00:00 Meet Kyle from Aleutian Adventures 02:12 Turning Adventure Into a Career 08:30 How Kyle Found His Way to Alaska 10:15 The Conference That Changed Everything 16:35 Betting on Yourself and Going All-In 24:45 Building a Career in Alaska's Fishing Industry 30:25 Control the Controllables 32:15 Hiring for Character, Not Just Skill 37:15 Leaving Alaska and Starting a New Chapter 42:20 Turning Patagonia Experience Into a Business Advantage 48:25 Marketing, Growth and Knowing Your Customer 56:00 Building a Career One Step at a Time 57:30 Choosing Family and Returning to Alaska 1:05:00 Getting Stuck in Argentina During COVID 1:14:00 Starting Over Again 1:18:30 The Opportunity That Became Aleutian Adventures 1:22:30 Rebuilding the Brand and Marketing 1:24:30 Why More Marketing Isn't Always Better 1:31:30 What's Next for Aleutian Adventures 1:34:30 Why Unplugged Experiences Matter More Than Ever 1:38:00 Protecting One of Alaska's Wildest Places 1:43:00 Closing Thoughts

Entrepreneurship Beyond Unicorns: Passion, Failure, and Fixing Mental Health with David Crane   Ken Okonek interviews veteran entrepreneur David Crane about myths of entrepreneurship, emphasizing that most founders are middle-class people working 80–100 hours and should pursue passion over money. Crane shares his healthcare-focused career, advice on finding passion by intersecting what you love with what you’re good at, and the importance of research, coachability, and building advisory teams to improve odds in a space where most startups fail. He describes learning through failure, managing founder anxiety by stepping out of the weeds, and the challenges of rapid growth. Crane explains his healthcare ventures focused on communication and care coordination, and his pivot into mental health after his sons’ struggles during COVID, including ListenRing for on-demand urgent mental health therapy and a peer-support platform for parents. Both discuss stigma, employer underuse of mental health resources, and giving back through volunteering.   00:00 Welcome and Guest Intro 00:45 Entrepreneurship Beyond Unicorns 02:31 Myths and Realities of Startups 03:42 Chase Passion Not Money 04:54 Finding Your Passion Sweet Spot 09:38 Turning Ideas Into Action 11:30 Overcoming Paralysis by Analysis 15:48 Failure as a Business Requirement 18:05 Advisory Boards for Growth 19:07 Healthcare Roots and First Venture 22:21 Care Coordination and Communication 23:18 Mental Health Pivot and New Platforms 27:41 Peer Led Advice 29:37 Liz Finds Support 31:15 Stigma And Pay 34:04 Workplace Stigma 36:07 EAP Not Used 37:59 Founder Anxiety 41:48 Panic Coping Skills 43:19 Owner To CEO 46:58 Managing Growth 50:02 Purpose And Giving 52:06 Wrap And Subscribe

Navigating the Cold Waters: Fred Drake's Snorkel Alaska Adventures Join Ken Okonek in this riveting episode of Kenversations: with Ken Okonek,' where he chats with Fred Drake, the visionary owner of Snorkel Alaska. Fred shares his incredible journey from learning scuba diving as a child, working on Norwegian Cruise Line ships, to pioneering snorkeling tours in the chilly waters of Alaska. Discover the unique challenges and exhilarating experiences that come with snorkeling in a place many wouldn't consider—a land of glaciers and cold water! Hear about Fred's most amazing encounters with marine life, the challenges of running a specialized small business, and his tips for aspiring entrepreneurs. Dive into this fascinating conversation filled with passion, adventure, and the beauty of Alaska's underwater world. 00:00 Welcome and Introduction 00:42 Fred's Journey into Snorkeling 01:55 Life on Cruise Ships 03:23 Transition to Alaska 06:04 Starting Snorkel Alaska 07:31 Challenges and Growth 16:07 Breaking Away from Cruise Lines 20:11 Going Independent 27:02 Transitioning to a New Partnership 27:31 Innovative Tour Ideas 29:51 Marine Life in Alaska 32:54 Logistics of Snorkel Tours 35:36 Memorable Encounters 40:30 Advice for Aspiring Entrepreneurs 43:50 Balancing Work and Play 49:23 Closing Remarks and Reflections

In this episode, we dive into the mindset and journey of Chad—how his personal story led to building a moving company that’s now dominating the industry in Alaska and expanding all the way to Idaho. Chad shares key lessons on growth, from mastering employee retention to creating a strong company culture that keeps teams engaged. One of his biggest insights? The power of self-awareness—knowing your strengths and weaknesses and delegating to those who can do it even better. This conversation is packed with wisdom for anyone looking to scale a business and build a winning team.

This one was a special one for me. Brady has been someone I have know from High school and we have walked in a lot of smilier paths and I just knew that it would be a good time. This man has done so many things and whatever it has been he has done it 100!  He gives massive perspective that will help you gain motivation to pursue things with an energy that gives you traction while getting a ton of joy while doing it.  We dig deep into what it takes to have fun learning again. We grow up in a society that really burns us out on learning and Brady has found a way to make that learning a passion that has led to massive joy in what he is doing and making a living while doing it and if you ask me. I can not think of a more admiral and impressive feat in this current day an age.  The meaning of life is to enjoy the passing of time and there are many nuggets in this one that I really think you will enjoy.

I have to first say how grateful I am to have Dan on my podcast and to call this man a friend. His journey and what he has overcame is hard to put in words. We go through his amazing background of video and cinematography and his passion for it and what pushes him to create amazing work.  But along the way life packs punches and Dan has had a few stack up along the way and he shares how he went through that process and what came out of it on the other side. He has turned in what I would imagine to be one the greatest pains and made it an amazing purpose that touches so many lives every day.    For anyone that has had hard times you need to take the time and litsen to the incredible mindset and wisdom that this man has to share.

Todays guest is Amanda Kramer she is a top business exec at a Fortune 500 company. Gartner is an information and technology company that is turning information into power when it comes to leadership and companies growing their business. We spend they entire podcast discussing. How she reached the C suite and what she contstaly coaches and mentors business leaders across the great state of Alaska.

Todays guest is Amanda Kramer she is a top business exec at a Fortune 500 company. Gartner is an information and technology company that is turning information into power when it comes to leadership and companies growing their business. We spend they entire podcast discussing. How she reached the C suite and what she contstaly coaches and mentors business leaders across the great state of Alaska.

Nate Is just a the most humble human you ever meet. He would never say how he leads 1000's of people to their financial and physical freedom and combat the thing we are all fighting which is aging. Nate has been a dear freind and close mentor of my in the world of leadership and coaching. He has grown and given so much to others and his team. We go deep dive into Identify and how one finds theirs or a process on how to refine it and grow it if you have not found that mission for yourself.  Next we talk about your perception and how to gain the wisdom to have the right filtering process of what to and how to listen to yourself and others.  Lastly we talk about culture. Which is totally a trending topic but given this post Covid pandemic world we live in. It is becoming a true lost art in what everyone needs in their own life, family, friends and work.

This one I am SO excited about! Today on Kenversations we had Pam Lloyd on the podcast. She is someone I wanted on here since day 1. She has been someone I have confided in many times in my life of transition.  Just a quick bit about Pam. She has been a lady that has not just climbed the corporate ladder she has Crushed it. So we dig into her story at many different levels and un-pack nuggets of gold for you all.  We go into how you need to be thinking and observing the world and environment around you to get to where you are to where you want to be.  Then right at the end in the last 30 minutes we had a complete tangent diving into the education system. Which I was so glad to do given Pam vast knowledge and first hand experience given her teaching back ground and working as a VP at GCI the biggest Alaskan company around. In teaching and tech.  We discuss our perspectives on what is going on currently where some pitfalls are and maybe some different ways to look at it or approach it in the future. I loved this tangent and I cant wait for you to all hear it.

I am so excited to share this one with you all! Chance was in the neighborhood so we had to have him on. We get to take a deep dive into another human living their best life. While he is pursuing his DREAM of being an North American Free Ride Pro. While going to school to be a MD.    We dig deep into his mindset and how do you prep and both mentally and physically to compete at the highest level. Chance is a wonderful human doing some intense things. Go check him out on Insta https://www.instagram.com/chancdp/

I cant wait for you all to listen into this one! Jake Sloan shares his journey to becoming a youtuber and business owner through his passions and things that bring him joy.  He shares some of the simplest yet profound nuggets of wisdom that have led to his successes and failures.  If you have any interest in creating a career out of your passions then this is the podcast episode for you.  I don't care if you want to be a landscaper or hairdresser or BBQ griller this man has the recipe that works for him and I am sure a few things will work for you.

Jon is back to talk more we dive deeper into the world of people with ADD and ADHD and how we process this weird world. We talk everything from sales and success to mindset and our past. We are who we are through nurture and nature.  Buckle up for a ping pong of back and forth and many subjects that we both found much common ground.

On this weeks episode of Kenversations I have the honor of interviewing Buddy Bailey. The son of Baileys Furniture that was dead set on going out on his own and pursuing a vision he came up with 14 years ago.  We talk the ups and downs of Buddy success and how he came to found Zo Financial. His ability to be a visionary and his motivation to create a product and company that will have a net win effect on the people all around us. A way for people to get by through tough times but also get the right support and foundation to get better credit and get out of debt and start to have a better relationship with money.  We talk a lot about what is driving him through the fear and scare of struggles of growing a new business that has had such insane growth in the last 3 years.  We did deep into the mindset of how you grow a company right. We talk about plenty of things "what not to do" In hope to inspire others and help them where they are struggling.  Buddy is an incredible leader, husband and Dad and what he is doing is going to have a great impact on his Legacy and those around him. I was grateful to have the time with him that I did.

How do you write a description for a man that Races one of the hardest races 5x in 5 years and then goes and decides to climb the 5 of the 7 tallest peaks across the globe and he only has 2 left to go and he will! Then on top of all that. He is a Dad and Husband to an amazing family. His kids are following his footsteps because of the trails he is blazing and just creating massive multiplication along the way. We dive into his mindset and perspective to take on some of the biggest and toughest challenges you can find while finding massive purpose and becoming a much better version of his self while he is at it. This man tapped into his deepest weakness and found a way to leverage his situation and gain absolute time freedom while he was at it.    You have to listen into this incredible hour of inspiration and mindset I challenge anyone to not be the most productive version of themselves after they get done. It will be physically impossible to be lazy or procrastinate while you are listening to this man inspire and impact so many.