Neil Patel

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From a humble beginning in South Africa to becoming a serial entrepreneur in the United States, Wayne Slavin’s story is one of perseverance, adaptability, and relentless pursuit of innovation. As a young immigrant in Southern California during the late 80s, Wayne experienced a world where possibilities seemed endless despite the initial challenges his family faced.

This backdrop of change and opportunity shaped Wayne’s entrepreneurial spirit and work ethic, leading him to build and scale multiple successful ventures. In this exclusive interview, Wayne talks about his 9-year journey as a founder leading up to building Sure.

Listen to the full podcast episode and review the transcript here.

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The Formative Years

Wayne’s early life in San Diego was marked by a unique blend of freedom and community. He recalls stories of empty freeways where cars would cluster together for company, a stark contrast to the bustling metropolis Southern California has become.

This period, coupled with the determination and grit of his immigrant parents, instilled in Wayne a deep appreciation for hard work and resilience.

His parents’ journey from South Africa to the US in the 80s, leaving behind everything to start afresh, became a cornerstone of his character and approach to business.

In Wayne’s opinion, the key is to share stories, knowledge, and the perspectives of each generation about moving to a new place and having an appreciation for the generations before you.

As Wayne notes, people’s stories repeat generation after generation, just as he did when he packed up his family during the COVID and moved to Texas. Moving to a new place and leaving everything behind takes a lot of grit and bravery.

Academic Pursuits and Early Ventures

Wayne pursued his undergraduate studies in San Diego and later attended Columbia University in New York City for graduate school. His passion for technology was evident from a young age, tinkering with DOS, dial-up connections, and bulletin boards, often breaking and fixing computers.

Wayne remembers how he eventually started to fix computers for not only his family but for other people also. The tech aspect came easily to him, and he always believed that the best product would win, but other things didn’t really matter. He calls himself a “tech beauty perfection purist.”

However, Wayne recognized early on that building and scaling a company required more than just technical expertise.

This realization drove him to study management, seeking to understand the intricacies of team building, culture creation, and the often unpredictable nature of human behavior in business.

As Wayne points out, management is more an art than a science. It is more situational than actually data-driven and empirical, which is code for product and things working together. People don’t always behave rationally; systems don’t always congregate around the most efficient solution.

You could learn how to manage things more efficiently and don’t see the need to get approval for technology. Wayne recounts a funny story from his undergrad year when he had to pass a mandatory technology course.

Wayne went up to the professor and told him he could either disrupt the class or correct him every time he made a mistake. Or, the professor could allow him just to show up and take the final.

Wayne ended up teaching the class for a whole semester, waking up at 7:30 am and leaving by lunch to go to his day job. The whole experience was similar to running a data center for a big startup in San Diego, proving once again that he didn’t need to get a stamp of approval to do tech.

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The Spark of Entrepreneurship

The entrepreneurial spark in Wayne was ignited by a simple yet profound philosophy imparted by his parents: if you want something, figure out how to get it.

This mindset, coupled with the early days of the internet, where innovative ways to make money were abundant, fueled his drive to create and innovate.

Wayne realized that everything is commoditized. Although they had tools like Shopify and WordPress, there were barriers to entry, so it came down to his determination to figure out how to overcome those barriers.

Wayne calls it his “imposter syndrome,” because every time something worked well, his instinct would be to go out and do it more, bigger, and larger. However, it always came with a big dose of skepticism about whether or not his ideas would work.

Some of them would have been more successful if Wayne had poured more resources into them. In his opinion, that’s essentially what management is all about—knowing when an idea is working and worth pursuing.

Bootstrapping His Early Ventures

Wayne’s ventures, from ad-driven models to SaaS businesses, were a testament to his ability to adapt and evolve with the changing landscape of technology and business.

Wayne’s initial ventures were bootstrapped, driven by an immigrant mindset of self-reliance and profitability. He was working out of Southern California, where the VC network had not yet taken hold and wasn’t part of the culture.

Wayne concedes that things might have been different if he had been in Northern California. Southern California is a great place to live and work, but the concept of venture capital is foreign and entrepreneurs would bootstrap their startups, which Wayne also did.

However, the concept worked because founders were disciplined in building a company and making it profitable. His first companies, built on ad-driven and SaaS models, taught him valuable lessons about market dynamics and controlling one’s destiny.

The first company helped cash flow, and Wayne bootstrapped the second, going from an ad-driven revenue model that was unpredictable. He realized that he wasn’t comfortable with Google being the overlord.

Google controls the clicks, the top of the sales funnel, and the cost per click. Wayne was not in control of his company’s destiny, which was his life’s theme and the culture he had instilled in his companies.

Ultimately, Wayne moved his company to the SaaS model at a time when SaaS wasn’t even a concept. Essentially, he was looking for solutions to get monthly payments without having to restart from the baseline.

Wayne points out that figuring out when to divert resources to a company is challenging or determining when the company has reached its ceiling and that his ideas have worked is challenging. In hindsight, his company had elite retention numbers and NRNs for a SaaS company.

These experiences laid the foundation for his future endeavors as he continuously sought ways to scale efficiently and effectively.

Going Back to Grad School

Wayne next decided to go to grad school in New York to get a change of pace. When he applied to the program, only 20 people were accepted. Wayne thinks that he got in because of an error in the system.

He wanted to join this particular program since they matched every student with a sitting Fortune 500 CIO or CTO of a big company, bank, private equity firm, or any other. Wayne wanted to be around a mentor who knew the venture capital world.

With this objective in mind, he tailored his thesis and coursework to attract a mentor. He was successful in his endeavor and now has an awesome venture investor on his company’s board.

Wayne wanted to do two things in parallel—go to school to learn to be a better manager and find someone knowledgeable about what he didn’t know. He wanted to learn from someone who had done it before instead of learning by failing.

Learning to Run Companies from Successful Managers

Wayne decided he wanted to learn from others how to manage a company, which is why he joined a big company, trying to go online and facing challenges along the way. This company later became a scaling SaaS startup, one of the biggest successes in New York tech history.

Wayne talks about how his experiences in the company helped him level up his skills. He watched great and terrible managers, the company politics, aligning incentives, and other aspects of the company.

Wayne was also a part of Buddy Media, which was later acquired by Salesforce, and Tapingo, which was bought out by Grubhub. He talks about how he worked for businesses like consumer electronics, enterprise software, and payments.

At Tapingo, they started food-ordering mobile payments on closed ecosystems that changed college campuses and the world of ordering food. Wayne was the VP of product before the company became Techcrunch’s most innovative company in 2013.

In the era before Snapchat, Amazon, and Tesla, the San Francisco company was doing amazing things and winning acclaim even though it hadn’t raised much capital.

Tapingo faced multiple challenges not just on the technical side of things but also on the payment and money aspect and selling to governments and universities.

The Birth of Sure

As Wayne reveals, when he started Sure, peak VCs were subsidizing Uber across San Francisco. At the time, any founder with an idea could raise seed capital and build a company. Once he had the idea for the company, it was impossible for Wayne to set it down.

The idea for Sure, Wayne’s digital insurance technology company, came to him in an unconventional setting—a turbulent flight to Las Vegas. Observing the fear and anxiety of his fellow passengers, Wayne wondered if he could sell life insurance to them in real time, right before takeoff.

Initially a joke, this thought evolved into a serious business proposition as he developed and tested a prototype. The overwhelmingly positive response to his initial tests, with a conversion rate of 16%, solidified his decision to pursue this venture.

At the time, Wayne knew nothing about insurance but knew about eCommerce and contextual commerce and was ready to leverage his experiences. He was unsure if people would buy insurance worth $50K or $5M and if they would spend $0.90 or $20.

Wayne also wanted to test if people would buy insurance a week or five hours before their trips. Or if they would buy for just one trip or a round trip. He had to figure out the price and product and collect data. He also spent a weekend testing the prototype.

Sure’s journey began with a mobile app designed to sell various types of insurance quickly and efficiently. However, through numerous meetings with major insurance companies, Wayne realized that the real value lay in the enterprise software he had developed to manage the business.

The Sure Business Model

Wayne started Sure based off of the idea that, eventually, insurance was going to come online. This insight led to a strategic pivot, focusing on providing SaaS infrastructure to run end-to-end insurance programs.

Sure works similarly to apps like DoorDash which display every restaurant on its interface. Sure provides users with detailed information about every type of insurance they can buy. They don’t need to re-enter their information but can avail of the automated service.

Wayne quickly realized that his management degree hadn’t taught him about aspects like marketing, customer acquisition, LTV to CAC ratios, and more. He ended up going through the process to see the C-Suite side of the company.

Wayne simply reached out to the major insurance companies in the US and asked them if they wanted to sell their product through the Sure mobile app. And that included home, pet, and travel insurance.

Next, Wayne provided them with a 30-second demo in which he demonstrated that purchasing insurance took just 30 seconds. He recalls traveling across the country, spending multiple days on the road.

Wayne realized that they were really good at building enterprise software, the distribution piece, and the customer acquisition piece. So, eventually, Sure evolved into a much more enterprise-focused infrastructure-focused application.

That’s how his InsurTech market unfolded, going from insurance companies that were trying to bring technology to where Sure is today.

Scaling and Success

As Wayne explains, the insurance infrastructure that they built is capital-intensive. Sure’s evolution into an enterprise-focused company has been marked by significant milestones and substantial capital raises.

To date, the company has raised approximately $123 million in venture capital, positioning itself as a pre-IPO company ready for the next phase of growth. Sure has received venture capital from traditional VCs and also corporate ventures in their space that understand the industry.

Storytelling is everything that Wayne Slavin was able to master. The key is capturing the essence of what you are doing in 15 to 20 slides. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend Peter Thiel (see it here), where the most critical slides are highlighted.

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Wayne’s emphasis on profitability, even in the face of substantial venture funding, reflects his commitment to sustainable business practices and controlling the company’s destiny. Sure’s success is a testament to Wayne’s vision, adaptability, and relentless pursuit of excellence.

He underscores the importance of capital efficiency and knowing the opportune time to scale and grow. He also talks about navigating the pandemic, four years of COVID furloughs, layoffs, poor profitability and ventures, and drying up deals and valuations.

Sure has positioned itself at the forefront of the Insurtech revolution by providing innovative insurance solutions through robust SaaS infrastructure, transforming how insurance is sold and managed in the digital age.

Wayne’s Vision for Sure

Wayne quotes McKinsey data and his real-world experiences with running billion-dollar programs. He reveals that nearly 1% of insurance transactions are done online without a single human involved.

The Internet has been on a mass adoption curve since 1995, and although it has been evolving for a long time, humans are involved in 99% of transactions.

An agent shows up at the customer’s house to examine the roof, pool, and fence, and another then enters information from one system to another for lack of automation.

In the next 10 years, drastic changes are going to come about. Wayne and his team have built a massive technology infrastructure requiring capital and pragmatism. Sure is essentially the visa of insurance and the rails to bring insurance transactions online between two constituents.

Insurance companies are underwriting and, in essence, issuing policies. Sure is enabling a new set of distribution for global Fortune 10 and Fortune 500 consumer brands that don’t sell insurance today to sell insurance.

Sure has helped the world’s largest EV manufacturer launch its auto insurance business. It runs the digital auto insurance business for the largest car manufacturer, Toyota. It enables it to do the same thing for small business insurance companies like QuickBooks and Mastercard.

Similarly, it provides the rails to run the embedded homeowners’ insurance program for online home lenders, Better.

Sure is at 1% adoption of insurance and will be truly online by 2030. Wayne estimates it to have 9% of insurance transactions, and aside from payments, insurance has the biggest dollar value in the biggest TAM in fintech. Sure is already running billion-dollar insurance programs.

Reflections and Future Aspirations

Wayne Slavin’s entrepreneurial journey is a powerful narrative of innovation, resilience, and visionary thinking.

From his roots in South Africa to his impactful ventures in the US, Wayne’s story inspires and exemplifies the transformative power of perseverance and ingenuity in the world of entrepreneurship.

Listen to the full podcast episode to know more, including:

  • Wayne Slavin’s immigrant background in Southern California instilled a strong work ethic and entrepreneurial spirit.
  • Wayne’s passion for technology started early, leading him to pursue education and hands-on experience in tech management.
  • His entrepreneurial journey began with bootstrapped startups, learning the importance of controlling destiny and profitability.
  • Wayne transitioned from bootstrapped ventures to seeking external capital and mentorship to scale businesses effectively.
  • His experience across consumer electronics, enterprise software, and payments led to the creation of Sure, a contextual insurance platform.
  • Sure evolved from a consumer-facing app to an enterprise-focused SaaS infrastructure provider for the insurance industry.
  • Despite significant venture capital raised, Wayne emphasizes the importance of profitability and financial prudence for sustainable growth.



For a winning deck, see the commentary on a pitch deck from an Uber competitor that has raised over $400M (see it here). 

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Neil Patel

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