Alex Matjanec of Wyshbox: “Understand why you need life insurance”

Understand why you need life insurance: When deciding what life insurance policy to choose, it’s essential to understand why you need it. Life insurance is not to make your family rich, it’s to fill the financial hole when you’re gone. If something happens to you, life insurance can allow your friends and family (and even […]

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Understand why you need life insurance: When deciding what life insurance policy to choose, it’s essential to understand why you need it. Life insurance is not to make your family rich, it’s to fill the financial hole when you’re gone. If something happens to you, life insurance can allow your friends and family (and even your pets) to live their lives how you had hoped they would. You need to ask “what would that cost?” And you’d be surprised that it may be less expensive than you think. Our research showed that people would save 40% on their life insurance if they really thought through where they would want the money spent.


As a part of our series about the “5 Things You Should Ask Before You Purchase a Life Insurance Policy” I had the pleasure of interviewing Alex Matjanec, Founder & Head of Purpose & Vision at Wyshbox.

Alex Matjanec is the Founder of Wyshbox and the CEO of String and Key. A successful CEO and serial entrepreneur for over a decade, Alex has led three successful companies that went on to be acquired. Alex has dedicated his career to empowering every person to have the full confidence of financial protection.


Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit. Can you tell us a story about what brought you to this specific career path?

It may be cliche, but I love solving problems. And when it comes to managing and protecting our money — I’m constantly asking “how can I make this better?” From investing, to saving, to insurance, I love to find ways to simplify a process that improves our quality of life and brings the best experience to customers.

A few years ago, I noticed that the life insurance industry was ripe for disruption. The process, the underwriting, the marketing, everything seemed ready for a tech upgrade. This is how Wyshbox came to be. Wyshbox is a modern life insurance provider that allows policyholders to create personalized and flexible policies in the form of “wyshes” to protect whatever they hold dear. Wyshes can be practical things like covering debts, to the non-traditional, like ensuring a cushy life for your pets or hiring your favorite musician to sing at your funeral.

Can you share a story about the funniest mistake you made when you were first starting in the industry? Can you tell us what lesson or takeaway you learned from that?

Our campaign for Wyshbox is called “What’s Your Wysh” — and we asked real people what kinds of things they’d like to protect if they were to pass away. The funny mistake I made was forgetting how “creative” the internet can be when a brand poses a question like that. Sure we got the traditional things like “I want my mortgage paid off” or “I want my daughter’s wedding paid for’’ — but we also got things like “I want to send a bottle of champagne to my neighbor who hated me” and “I want a full-time person to rub my pet pig’s belly.” We learned very quickly how personal people were responding to our campaign, and that we should look to embrace these types of stories and make them the hero. These stories became the content we share on TikTok.

Are you working on any exciting new projects now? How do you think that will help people?

Yes. We officially launched our Wyshbox app in mid-September, and our goal is to empower consumers to be financially responsible and protected in an easy, simple way. We plan to continuously redefine financial protection, and we have projects in the works to expand on this. We are always improving our app, our underwriting and trying to keep the life insurance sign-up process simple and accessible.

We just successfully launched in ten states and will continue to expand within the United States throughout the year. We are hyper-focused on providing our customers access to affordable, customizable life insurance and honor their wishes once they have passed.

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Is there a takeaway or lessons that others can learn from that?

I’ve had two major “Aha moments” in my career. The first was recognizing that solving a problem was more important than picking a particular industry. I chose to work in the fintech and insurance industry because it was ripe for change. I saw an opportunity to take something that was purely transactional and make it engaging, supportive and accessible to everyone.

The second, was finally recognizing when I was stretched too thin. When leading two growing companies, I couldn’t give both companies the attention they needed. I simply didn’t have enough time in the day. My co-founders and I decided to split the companies so I could take a step back to lead the business that needed my attention. That company eventually built and launched Wyshbox.

What advice would you give to other people in the insurance field to thrive and avoid burnout?

Have clear expectations before you begin a career in the insurance industry. It’s important for new insurance pros to recognize that the industry is incredibly hard. Be prepared to do the leg work.

Be an infinite learner. Learn from people who have been in the industry for years. Love the industry and take the time to gain experience.

Ok, thank you for that. Let’s now shift to the main focus of our discussion. As an “insurance insider”, you know much more about insurance than most consumers. If your loved one wanted to buy a policy from another person, which 5 things would you advise them to find out about before committing to a policy? Can you give an example or story for each?

  1. Understand why you need life insurance: When deciding what life insurance policy to choose, it’s essential to understand why you need it. Life insurance is not to make your family rich, it’s to fill the financial hole when you’re gone. If something happens to you, life insurance can allow your friends and family (and even your pets) to live their lives how you had hoped they would. You need to ask “what would that cost?” And you’d be surprised that it may be less expensive than you think. Our research showed that people would save 40% on their life insurance if they really thought through where they would want the money spent.
  2. Find an insurer that’s flexible: Traditional life insurance is purchased in a way that you are buying more coverage than you need to, with the idea that you will grow into it as you get older. Instead, look for an insurer with flexible, adaptable rates that will be cost-effective down the road. Your insurance should be suited to where you are now, not where you may be later in life.
  3. Look at reviews more than price: Before selecting a life insurance company, do your due diligence. Look at their reviews and their rankings. Gauge their customer service when you chat with them on the phone. At some point, you or your beneficiary will need to rely on them. Trust is essential.
  4. Make sure your loved ones get paid: You need to understand every scenario that could jeopardize a life insurance payout. If you die skydiving, will you still get your money? Ask these questions.
  5. Know the Lingo: Take time to learn the terminology of insurance, like the difference between whole life versus term life. One is more expensive but creates a cash value. The other has no cash value. Be completely informed.

Insurance agencies or companies are often known to be very creative and innovative marketers. Do you use any clever and innovative marketing strategies that you think large legacy companies should consider adopting?

Yes. A digital insurance company like Wyshbox gets to tell a story about the amazing experience of our platform, like how easily you can adjust your policy, and how amazing our customer service or “Wysh Granters” are. By being more Ingrained in the insurance experience, we can use creativity and humour in our campaign to move the conversation beyond a transactional product. By leveraging platforms like TikTok, Instagram Stories, Spotify, Reddit, and streaming platforms, we can be where our audience is, with a story they are interested in.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

One person who has been extremely influential in my career is an entrepreneur named Steve Minichini. He took me under his wing and gave me the confidence to take risks and trust my gut. He encouraged me to be bold and go after my ideas. He guided me from a work and personal perspective.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I am Canadian, and as a Canadian I grew up with universal healthcare. It’s a different story in the US. As an entrepreneur and business owner, my contribution to society is to build a business that reflects what society could and should look like. As Wyshbox grows, I want to provide free healthcare, phenomenal benefits and free transportation to my team. We can be an example to other companies that can then follow our lead. This is the movement I would like to start.

How can our readers follow you on social media?

Feel free to follow me on LinkedIn, and keep up with Wyshbox on our website.

Thank you so much for sharing these important insights. We wish you continued success and good health!

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