Aaron Shapiro is the founder and CEO of life insurance company Dayforward. He is also an “entrepreneur, marketing executive, and investor based in New York City.”
As an entrepreneur, Aaron Shapiro has more than a decade of experience in starting and running businesses. In 1999, he was co-founder of the “email marketing software company Silverpop.”
In 2005, Aaron Shapiro was one of the four co-founders of the “experience design and digital marketing agency” Huge. He also became CEO of Huge in 2010.
Likewise, Aaron Shapiro was also a co-founder and chairman of Honey, an “enterprise communications startup” based in New York City.
According to Aaron Shapiro, Dayforward plans to “modernize the insurance industry by cutting out the middleman and allowing customers to buy directly from the site.” This venture has been in the works since 2018.
Aaron Shapiro said he “wanted to focus on a kind of problem that would have a really big societal impact.” Since his company offers DTC life insurance, he hopes that more people can access it.
Currently, Dayforward has a license to sell life insurance in Texas. However, Aaron Shapiro plans to expand nationwide over the next two years.
In 2011, Aaron Shapiro was named one of the 40 Under 40 by Crain’s New York. He also wrote the book Users Not Customers, published by Portfolio/Penguin.
Check out more interviews with insurance innovators here. You can also buy Aaron Shapiro’s book here.
Everybody in this industry sells the same exact products. Aaron Shapiro, Dayforward
Jerome Knyszewski: What do you think makes your company stand out? Can you share a story?
Aaron Shapiro: I think that one of the most significant trends when it comes to digital businesses is that companies are weighing on increasingly verticalizing their business, meaning they control all aspects of the value chain.
From DTC’s that cut out the middleman to major brands like Nike moving away from retail and selling more of their products directly, companies are embracing the fact that controlling the full value chain allows you to produce a much better customer experience.
However, this is still a relatively new concept in the insurance space. Here, you still have brokers, you have agents, and you have customers who are not being well served.
Everybody in this industry sells the same exact products.
The fact is, this is a commoditized space where the whole industry relies on brokers price shopping on behalf of their clients.
And we’re saying that’s the wrong model because we can make a better product and nobody’s doing that in this space.
The fact that we’re a fully verticalized provider means we can create a truly great experience for our customers and build rewarding relationships with them.
It also means that we can create better products that are really custom designed to our consumer’s needs.
Jerome Knyszewski: Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?
Aaron Shapiro: That’s such a hard question to answer, because I generally think that making mistakes is the best way to learn. Good things can even come from bad advice, so I don’t think of it as things I wish I’d done, I just think of the things I’ve learned.
I can also admit when I’m wrong, and not get entrenched in an idea just because it was my original vision.
Jerome Knyszewski: You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Aaron Shapiro: I think a certain curiosity about the world and how things work, as well as the ability to really listen have been important in my career. It helps me understand that the market tells you the answers, and not the other way around.
I can also admit when I’m wrong, and not get entrenched in an idea just because it was my original vision. I mean, building a greeting card company that became a serious marketing SaaS solution is a pretty good example of that!
There seems to be this myth of the “visionary entrepreneur” who just has all the answers. I don’t think that’s entrepreneurship in real life.
I think it’s really about deeply observing things and learning and understanding and being open-minded enough to change course when it’s time.
If you’re not able to be agile and learn from what’s happening around you and what the market is really looking for, it becomes much easier to fail.
Jerome Knyszewski: Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?
Aaron Shapiro: Stay curious! Try to do things that are intellectually stimulating to keep your mind active. If you’re ever having doubts or feel stuck, don’t be afraid to try new things, new approaches, new angles, or try to think about a problem differently.
I think one of the most common mistakes is trying to do too much in either direction.
Jerome Knyszewski: What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?
Aaron Shapiro: I think one of the most common mistakes is trying to do too much in either direction. Sometimes I see entrepreneurs trying to do too many things, and they all end up half-baked.
Other companies are so stubborn that they don’t want to change, and that CEO just goes down with the ship. It’s a tricky balance of finding your focus, yet being able to pivot thoughtfully.
For me, the key to building a strong company is doing one thing really well, having the discipline to figure out what exactly that is, and then being willing to learn as you grow.
Jerome Knyszewski: In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?
Aaron Shapiro: Hiring the right people! I think the ability to delegate is one of the most underestimated skills, and something a lot of CEO’s miss the mark on when they’re launching a company.
The role of a CEO is to direct the company and facilitate the opportunity for good things to happen. When you hire the right team, you give the company, and yourself, the best chance to be truly successful.
Climate change affects not just our future, but our health, our security, and our economic equality. Aaron Shapiro
Jerome Knyszewski: You are a person of great influence. If you could start 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. 🙂
Aaron Shapiro: I believe that climate change is the most important issue we have today. Of all the problems we’re facing, it’s the one that fundamentally threatens our existence.
Climate change affects not just our future, but our health, our security, and our economic equality.
Because I don’t personally have the tools to fix climate change (I wish!) I tried to tackle one piece of that puzzle by making protecting families and helping them feel more secure about the future my personal mission.
Jerome Knyszewski: How can our readers further follow you online?
Aaron Shapiro: You can visit Dayforward on our website to learn more about Dayforward life insurance, and follow us @dayfwrd on Instagram, Facebook, and Twitter.
Jerome Knyszewski: This was very inspiring. Thank you so much for the time you spent with this!
