Chief Change Officer - #378 Ral West: From Charter Planes to Real Estate Empires—Systems, Grit, and Reinvention

Episode Date: May 17, 2025

Most people retire after one successful business. Ral West kept building.In this episode, Ral shares how she co-ran a charter airline between Alaska and Hawaii for 25 years—eventually selling it to Alaska Airlines—and then launched into her next chapters: owning cruise ships, investing in real estate syndications, and helping other entrepreneurs find sustainability without burnout.From navigating gender bias in a family business to designing automated booking systems and letting go of control through delegation, Ral’s story is a masterclass in evolving through every season of life. Whether you’re in the startup grind, planning an exit, or rethinking what “retirement” means—her story will get you dreaming smarter and bolder.Key Highlights of Our Interview:The 25-Year Flight Plan: From Tourism to Aviation“I started in Alaska tourism. My husband was in real estate. Together, we launched a charter service to Hawaii—and turned it into a full airline.”Selling to Alaska Airlines: A Strategic Exit“We knew they were entering the Hawaii market. Instead of competing, we showed them why buying us was smarter.”When Cruise Ships Became the Next Chapter“We bought five small cruise ships out of bankruptcy, redesigned the Alaskan travel experience—and then pivoted again after COVID shut everything down.”Why Real Estate Was the Right Post-COVID Play“We own part of over 6,000 apartment units in five states. Why? Because homeownership is becoming harder, and rental demand is rising.”From Exhaustion to Empowerment: Lessons from the Middle Years“Between 35 and 55, I was stretched thin—business, babies, burnout. I had to build systems and teams to stay afloat.”The Real ROI of Delegation“Delegation isn’t about giving things away—it’s about building trust and giving others space to shine.”Turning Intuition into Systems“I realized I made ad-spend decisions based on 3-day sales trends. Once I named it, I turned it into a repeatable formula my team could follow.”Reservation System Reinvention“We invested two years into building an online booking system that ran 24/7—freeing us from the phones and doubling our revenue.”Not Your Typical Retirement Plan“I could’ve retired 16 years ago. I didn’t. I love working. My retirement plan is doing what I want, when I want, with the systems to support it.”Advice for Entrepreneurs at Any Age“Be bold. Stay curious. Watch the world. And don’t let age—or fear—be the thing that keeps you small.”______________________Connect with us:Host: Vince Chan | Guest: Ral West  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.17 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1.5% Podcast.Top 10 US Business.Top 1 US Careers.>>>160,000+ are outgrowing. Act Today.<<<

Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Oshul is a modernist community for change progressives in organizational and human transformation from around the world. Today's guest, Raelle West, is the kind of person you meet and immediately think, wow, she has lived such a full life. Over 40 years as an entrepreneur, her story is full of twists and turns. In her mid-twenties, she took a leap and started her first business. That was just

the beginning. For 25 years, she to Alaska Airlines, a huge milestone, but not the end of her journey. She has owned small cruise ships, invested in real estate, invested in real estate and kept building. And now she's helping other women entrepreneurs figure out the same thing she did, how to run a business and have a life with sustainability. Her story is real and packed with lessons for anyone chasing big dreams. Let's dive in. Well, good afternoon.

Welcome to our show. Welcome to Chief Change Officer. You and I have the longest time difference, 17 hours. Thank you for coming on board. Thanks, Vince. And I love the distinction of the time difference. Time difference reflects distance. Thanks Vince, and I love the distinction of the time difference. Time difference reflects distance. So far, among all my guests, you are the most distant one. The very first guest from Alaska.

I've never visited Alaska. The closest I've been was a transit stop when flying from Asia to Toronto, Canada. But now I finally have the chance to connect with someone from Alaska. I'm so excited to learn more. Let's get started with your story. Walk us through your career journey, your history, the major transitions, and the key moments of evolution. Then we'll explore different elements in our conversation. Okay, Vince, in a capsule, 40 years plus I've been an entrepreneur.

And before that I grew up in an entrepreneurial family. So I think it ran in my blood. So in my mid twenties, I opened my first business and went on to have a serial entrepreneur, if you will, had many different businesses. And the primary business was one that I ran with my husband. And we ran the business for 25 years. It was a business that operated charter air service between Alaska and Hawaii with wide body jets. And after 25 years, we were able to exit the business by selling it to Alaska Airlines. And in other career pivots, since then, we have owned small cruise ships, we have invested

in multi-family real estate syndications, and we are still doing that. So a varied career for, as I say, over 40 years. And that brings me to today, where I have yet another business that I've started, where I would teaching entrepreneurs how to accomplish what I have in that you can run your business and have the life that you want at the same time. You mentioned you grew up in an entrepreneurial family. So that vibe, the mindset of building and creating was part of your education from an early age. Then in your 20s, you stepped into the game yourself, starting your own ventures. You've been involved in various businesses since.

I'm curious, how do you decide which area to focus on? Is it a lot of strategic calculation, following trends, gut feeling, or just going where the money is. What's the thought process when choosing a business to start or invest in? And what lessons have you learned along the way? To start with, I was raised in a tourism family. So that was my initial business was related to tourism. And I was helping businesses with

their marketing and advertising businesses that were involved in tourism in Alaska. I wasn't born in Alaska. I was born in Seattle, but I moved to Alaska in my twenties and that's where I decided to launch out onto my own because I saw an opportunity and I think that's the main criteria, is that there was an opportunity because there were many small tourism businesses that didn't know how to get their product out to market. And I had the experience doing that

in the work that I had already done in tourism. So I thought, I can offer them this service and I can provide them with what they need to get their product to market. So I did that to begin with. Then the business that my husband started was a spin-off of that. He was in real estate and he decided that he wanted to make these free trips to Hawaii like I was doing because some of my clients were in Hawaii and she said,

okay, I'm going to represent Alaskans who own condos in Hawaii, and I will work at the condos for them. Then I added to that with, okay, but you need to also add the rental cars and the air and make a whole package out of it, because that was my experience in tourism, so you need a whole vacation package. So together we built that company and it was basically a merger of his expertise with my expertise and we ran with it. Along the way we started investing in some real estate just on the side and later on when the time came to sell the business that opportunity arose because we knew that Alaska Airlines was planning to enter the Hawaii market and we knew that their pockets were deeper than ours and it just made sense for them to buy our company rather than for us to duke it

out in the marketplace and we both lose a lot of money. So we convinced them that buying our business was a lot cheaper than winning the market from us. So the pivot that came next was again a spinoff because my family's business that I had not been involved in personally for several years was involved in small cruise ships in Alaska. And we had a different idea as to how to present cruises to people visiting Alaska. Instead of just going from port to port, we felt that they would have a better experience of Alaska by leaving from a port and going out into the wilderness, getting onto a skiff and playing with the whales, going kayaking, going ashore and taking hikes

in the forest or even walking on a glacier. And these things were things that we were enjoying on our own boat in Alaska, because by that time we, my husband's a boataholic, so we had to have boats up here. And so we found a couple of cruise ships that were bank owned. They had been owned by a company that went bankrupt. And so the bank held them and they were sitting at a dock rotting. So again, it was an opportunity. And we seized that opportunity and bought those ships out of rather low price point and fixed them up and found somebody to operate them for us. And then later there was another company that went bankrupt and we bought some

more cruise ships. So we ended up having five small cruise ships under a hundred passengers each that were operating in Alaska and providing the kind of adventure, the wilderness experience that we felt that people would really enjoy in Alaska. So that lasted for about 10 years and we were selling the vessels one by one to the company that operated them. But COVID happened then. We had one ship left and it got tied up to a dock because no cruise ships were operating anywhere in the world.

So that was a pretty obvious sign to us that it was time to pivot away from cruise ships until we sold that last ship. And then we spent a fair amount of time studying the landscape of world economy. Where were the opportunities? Where was the world going next? What would be the outcome after COVID? We would listen to podcasts, and we would read. We would attend workshops.

That's when we decided that the future seemed to be in going in the direction of real estate and particularly multi-family real estate because buying an individual home was becoming more and more cost prohibitive, which meant that people were going to be renting. So we decided that that would be a good place to put our money. And we started investing as a general partner, limited partner, in various syndications, where we were involved in purchasing complexes that had a hundred or more apartment units in a complex. And we now own over, or we're part owners anyway, in over 6,000 of these apartment units in five states across the U.S.

So it's a combination of seizing opportunities, but also just keeping your eyes on what's going on around you. The world is changing all the time. And if you're not staying aware and keep your eyes open to what's going on around you, you can miss some of these opportunities. So that's the main key. what's going on around you, you can miss some of these opportunities. So that's the main key. I see you as a very successful self-made business person, someone who has steadily built wealth

over time with discipline, whilst building opportunities along the way, how would you describe your approach? In your own words, what kind of business person are you? I think that I definitely am a risk taker, and that comes from my family culture as well, coming from the entrepreneurial background that I have. But I do take calculated risks, and I from the entrepreneurial background that I have. But I do take calculated risks and I do the homework and I run the numbers and I do some research and investigate the market.

And I've learned along the way because sometimes I didn't do my research and my homework as well as I should have and that was a big learning experience that was painful. So I don't want to do that again. And then now in this particular, my newest business, it's more of, as you said, making a contribution and giving back and sharing my years of experience and knowledge with entrepreneurs so that I can offer them the guidance and the wisdom and help them cut out a lot of the pain and learning experiences that I had, make it easier for them.

In your entrepreneurial journey as a woman, have you faced challenges that might differ from those faced by men in similar positions? I ask because even today, in a tact-driven world, it is well known that women, regardless of age, still face unique hurdles. For instance, female tact-bounders struggle with raising money as easily or in the same amount as their male counterparts. Reflecting on your experience across the different businesses you've built and run, what were some of the key challenges you've encountered as a woman business leader?

as a woman business leader and now as a coach, how do you guide younger women to navigate and overcome similar challenges learning from what you faced and learned? I think that early in my career actually when I was working for my father I experienced more of the glass ceiling and the prejudice against women and once I went out on my own and said yeah thanks dad I'm gonna do this myself then I was able to break away from that because he was a bit chauvinistic he came from another generation and so I said not not going, I'm not dealing with that. I didn't really experience too much in the way of discrimination or any obstacles because I was a woman.

I think I, maybe I just had a lot of confidence and I just didn't let it stop me. I was just braring to go and I just knew that I could do a better job than most anybody else let me at it. So I'd say that for women, all women, whatever age, you have to believe in yourself and you have to have the confidence that you know what you know and you can do the job. I think that women, when I was between 35 and 55. I was juggling young children and a business and volunteer activities and I was exhausted and overwhelmed and I was stretched so thin. Sleep

was a luxury and I the relationship with my husband suffered and my health suffered and I just couldn't do at all. So I think that I can relate to women who are in that period of their lives where they're trying to juggle so many things. And what I learned the hard way was how to create the systems and the processes and build a team around me, use leverage and get out of that stress and overwhelm by building a real system and structure around me so that I could operate the business whether I was there or not. And I developed metrics and data-based management and it all allowed me to have more freedom to do what I wanted to do. So by the time I was about the end of that time period,

by the time I was 55 and the kids were grown, I was able to take off and do whatever I wanted to do because I had a team in place, I had managers in place. I was free. And that's what I would like to share with other women that they can do that too. Doesn't matter if you're male or female, so don't let that stop you. So that's what I would give as advice to any woman.

How do you guide people in building the kind of system from ground up? Specifically, how do we teach them to lay the foundation, develop the structure, and ensure is resilient enough to grow and thrive before they can step back and enjoy the fruit of their labor? The creation of all of the systems and the processes and building the team happened over a period of years. It was certainly not an overnight transformation and I had to learn a little bit by little bit by reading books and actually went back to college and studied with people like Robert

Kiyosaki and read books like the E-Myth by Michael Gerber. And I learned bit by bit how to establish written procedures for every job. I learned how to write down what it was that I do so that I could teach someone else how to do it. It didn't really need a tremendous amount of financial success in order to learn how to delegate. Even if you're a solo creneur, you can hire a very inexpensive virtual assistant

or part-time help to just take some of those tasks off your plate. So you need to really chunk it down into bite-sized pieces of what you do every day and what of those things that you do could be easily transferred to someone else to let them do it. And one of my challenges was also to figure out what my decision-making process was so that other team members could make decisions

even if I wasn't there. That was more complicated because how do you chunk down and turn into a written process, how you made a decision about, for example, when to spend more money on advertising. And that was a very complicated thought process to come to that conclusion. And after a few weeks of trying to figure it out,

I decided that I was watching the metrics of the sales and I, and I was able to discern that if the sales were decreasing, like over a period of three days, that meant we needed to beef up the advertising, but you need to be able to document all of these things. And that takes time to be introspective and figure out how it is that you're running this business and get written policies, procedures, training manuals, build a team, train the team, create a company culture that embodies everything that you feel is important, your values and your principles and have that carried

out throughout the organization. And there are just so many aspects we needed to improve our customer service. We needed to make sure that we were collecting feedback from our customers so that we could provide the level of expectation that they wanted. And because we depended on repeat business, if we didn't keep our customers happy, we wouldn't get that repeat business. So there were so many aspects to it. And we had a team of two or three or four dozen people. So it wasn't a huge business,

but it wasn't real tiny either. And I had the ability to delegate and create processes and systems with our teams. Could you share some specific examples where you built a base for yourself. There are many examples. I'm trying to call the one that would be the most relevant. And I think one thing that might be relatable is that our business involved taking reservations

for our air service over the phone. So we had reservations agents who would answer the phone and take a booking by using our in-house computer reservation system. And no booking was taken without somebody being on the phone to take that booking. So as time went on, we were realizing that this was not a very efficient system. And we invested a huge amount of money and almost two years to develop an automated reservation system. And that system, once we pulled the trigger on it and it went live, it was able to take

the bookings 24-7 without any of our reservation agents talking on the phone at all. Whether you are a travel agent or a customer, you could go online and book your trip entirely online. That was a huge transition for our company and it made a gigantic difference in our revenue by being able to automate that reservation system. So just like with what you're talking about in terms of your podcast,

the more you're able to automate some of your processes so that you can repeat your systems over and over again in less and less time, that enables you to increase your productivity and hopefully your revenue as well. You've reached a point where traditionally you could retire, stop working, travel around the world, dive into hobbies. But the concept of retirement has changed. In today's world, it's not always about stepping away completely. I'm curious, what's your personal take on retirement? Would you consider retiring in the conventional sense? Or do you have a different vision for this stage of life?

I think I'm a bit different than a lot of people. Financially, we could have retired when we sold our business to Alaska Airlines, and that was like 16 years ago. But we had still a lot of energy and ideas, and we didn't want to retire. So I think our decision to not retire was based on just our own motivation and desire and interest. So particularly, I am continuing to work just because I love it and I don't feel the need to sit back and I do love to travel. My definition of

living the dream is being able to travel the world. We take long trips. I recently got back from a six-week trip in Europe and I plan to do a lot more of that. I love cruising and I don't intend to give that up but I also don't intend to give up my business. So I have to figure out a way to have the businesses run very smoothly and with these processes and systems going, whether I'm around or not. And so my definition of retirement is just living the life that I want and having whatever business I want to have. I don't need it for monetary reasons. I just want it because it's my passion. It's my joy.

And I don't see that age has any bearing on whether or not I continue to work. You know, long as I love it and I can do it, I'm going to. The idea of retirement is evolving rapidly, is no longer about just stopping work and living off savings or pensions. Financial independence now means people have choices, whether to keep working, pivot into a passion project, or even take breaks to recharge and come back stronger. From your perspective, with financial freedom at your disposal, how do you view retirement? When you think about this for the border population, how do you see the concept shifting?

If we put on the futurist hats, where do you think retirement is headed in the next decade or two? I'd love to hear your vision for how this concept may evolve. I think that people need to be able to pivot and that the pivot will depend on what their inner desires and motivations are. And I think that I personally am an advocate of people following their heart and following their passion. If they love what they do, why not keep doing it? Financially, I think it's great to make sure that you have a consistent source of income, whether that be some kind of

retirement account that's generating some income for you or you have passive investments like our real estate, they are considered passive investments because they earn money while we're sleeping. So that's an important aspect of being able to be financially independent and live the life the way you want to live it, whether that means working or not working. We have friends who are just totally enjoying their retirement. They have the financial means to do what they want and they travel or they play golf or

pickleball or do volunteer work, whatever they want to do. And I think that the traditional definition of retirement of reaching age 65 and then you quit your job that you've had for 30 or 40 years and you're hanging up and go home and sit on the couch, that's gone. I don't see that happening. I think that people can reinvent themselves and develop new ways to keep themselves occupied and follow a passion and maybe that passion will be generating some income or maybe it won't.

But you do have to have some financial wherewithal to be able to live the life that you want. I think that's important. I think that people nowadays have an opportunity to create so many more opportunities for themselves and there are really no limits. You mentioned AI earlier and with the digital age, there are just so many things that people could do, so many opportunities. If you look around and see what,

where people need to be served and you can provide that service, why not do that? And be creative, be bold, be confident, and don't let your age or your situation stop you. And I just believe that people need to go for it. That would be my final word. Thank you so much for joining us today. If you like what you heard, don't forget, subscribe to our show, leave us top-rated reviews, check out our website,

and follow me on social media. I'm Vince Chen, your ambitious human host. Until next time, take care.