Aaron Shapiro, of Dayforward: “Failure Is Your Friend”

by Jerome Knyszewski
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Aaron Shapiro Dayforward

Founder of Dayforward Aaron Shapiro is also the company’s chief executive. He has years of experience as a founder and business leader.

Before Dayforward, Aaron Shapiro worked for 13 years as the founder and CEO of Huge, which is a “1,500-person global digital agency that was sold to IPG.” He’d also founded and ran Silverpop, a “marketing automation SaaS that was sold to IBM.”

Also prior to Dayforward, Aaron Shapiro “started IPG digital agency” Elephant, as well as Honey, “a modern intranet.”

Aaron Shapiro founded Dayforward in late 2020. The company has received a license to “sell life insurance in Texas with plans to expand nationwide over the next two years, with availability in new states every few months.”

Likewise, Aaron Shapiro and Dayforward plan to “modernize the insurance industry by cutting out the middleman and allowing customers to buy directly from the site.” He has been working on this capability since 2018, when he left the agency world.

At Dayforward, Aaron Shapiro said he “wanted to focus on a kind of problem that would have a really big societal impact.” He understood that “getting life insurance can be a muddled process,” resulting in only a few people getting it.

With Dayforward, Aaron Shapiro hopes to make life insurance accessible to more people.

Check out more interviews with insurance executives here. You can also check out Aaron Shapiro’s book Users Not Customers here.

Suddenly I could see that there was a total disconnect in life insurance companies, where they see the people selling their products as their customers over the people who are buying policies. Aaron Shapiro, Dayforward

Jerome Knyszewski: Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Aaron Shapiro: I’ve spent my career building companies in the technology and marketing space. My first company, Silverpop, was sold to IBM in 2014.

After that, I co-founded and served as the CEO of Huge, where I focused on digital consulting and helping brands innovate in the online space.

Today, I’m the founder and CEO of Dayforward, which I’ve been building for the past two years.

I first got interested in the life insurance space because we had clients in the life insurance industry at Huge, and it gave me the opportunity to see how things were being done.

I learned a lot about the sector and where the opportunities were, and I thought it would be an exciting industry to found a startup that could create a very different approach to life insurance.

Jerome Knyszewski: What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

Aaron Shapiro: I remember one meeting where I was having a conversation with a client in the insurance space, and I was talking about customers and user experience and how important it was to be customer-centric.

As we were talking, I realized that when they used the term “customers,” they were talking about agents and brokers, while I was talking about their policyholders.

Suddenly I could see that there was a total disconnect in life insurance companies, where they see the people selling their products as their customers over the people who are buying policies.

That moment really crystallized the problems with this industry for me, and how a truly customer-centric approach could do a better job protecting families.

Then I reflected on my personal experience buying life insurance and the challenge so many families have in building financial security for their family, and I started thinking about all the things we could do to make it better.

We’ve already seen a lot of excitement and enthusiasm, especially from our target market of young families.

Jerome Knyszewski: Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Aaron Shapiro: This is a more recent example, but we were thrown a real curveball when we started Dayforward. Just as we were gearing up for fundraising and hiring the next set of employees, the pandemic hit.

Almost overnight, we went from a place of excitement and optimism to wondering just how long this was going to last. We had investors tell us “we’ll just wait to meet you next month,” but that was in mid-March, so obviously that never happened!

Suddenly, we had to figure out how to pitch to investors over Zoom and build a company without being able to meet face to face.

If there was a silver lining to everything that happened, it’s that the pandemic really drove home the importance of life insurance and financial security, and that even became a rallying cry for the company.

Jerome Knyszewski: So, how are things going today? How did your grit and resilience lead to your eventual success?

Aaron Shapiro: We found our footing and eventually adjusted to a fully remote model. We launched in Texas (our first market) in January, and are planning to expand nationally soon.

We’ve already seen a lot of excitement and enthusiasm, especially from our target market of young families.

Dayforward is actually uniquely suited for this “new normal,” with an automated purchasing process and at-home health kits to keep the process streamlined and safe, so we’re confident in our ability to really impact the lives of American families, both during the pandemic and beyond.

Honestly, every one of my companies has faced adversity, starting with the dot.com crash. I struggled in 2007 when the financial crisis hit — a lot of our competitors went out of business because they weren’t prepared for the aftermath.

But I learned the importance of reacting quickly and striving to always be more prepared than you were the last time, and that’s one reason I’ve been able to keep moving forward.

Jerome Knyszewski: Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

Aaron Shapiro: I don’t know if it’s a mistake, per se, but my first company Silverpop was actually focused on creating electronic greeting cards. It was the early days of the internet, when people were sending Happy Birthday emails with dancing pineapples or whatever animation they liked.

At one point, Silverpop became one of the top 500 sites on the internet — that shows you how small the web was back then! Eventually we started to see that people were using our greeting cards as regular communications, but with animations (similar to how we use emojis today).

At that point, we pivoted to working with companies and building out the marketing animation capabilities, the technology for which was eventually sold to IBM and became the building blocks to Watson AI.

So it became something really serious, but it started out as a completely lighthearted way to entertain people.

There’s a saying that some people are “an overnight success ten years in the making,” and this is especially true for entrepreneurs. Aaron Shapiro

Jerome Knyszewski: Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading My Company”? Please share a story or an example for each.

Aaron Shapiro:

  • Failure is your friend. There’s a saying that some people are “an overnight success ten years in the making,” and this is especially true for entrepreneurs.

Most ideas will fail, but it’s your ability to learn from those failures and persevere that will determine how     successful you are.

  • Your relationship with money might need to change. Before you raise money, funding is the limiting factor to growing the business.

    But once you have the capital, talent and hiring great people becomes the limiting factor.

  • Know your role, and don’t micromanage. Your company will outgrow you if you can’t learn to let go and trust your team.

    The job of a CEO is to hire the right people and create the tools for them to succeed, so don’t get caught up trying to do everything yourself.

  • Embrace constraints. If you had told me a year ago I would have been pitching investors and launching a startup without the ability to meet anyone in person, I would have thought you were crazy.

    But our team has been able to thrive virtually in ways we never could have expected.

  • Flexibility can be more powerful than your vision. You might think that you have the perfect vision to create a company, but in reality, the market tells you what business you’re in.

    The ability to be flexible and make adjustments as you go (even when those adjustments aren’t in line with your original intent), can be the difference between failure and success.

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!


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