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He Sold His Business And Then Raised Over $100 Million To Disrupt A $100 Billion Industry

Alejandro Cremades
Assaf Wand

Assaf Wand is a true serial entrepreneur with many launches and exits. His most recent venture, Hippo Insurance, is taking on a $100 billion market, with very large, well funded and entrenched competitors. Yet, they are gaining great traction.

Assaf recently appeared as a guest on the DealMakers podcast. During the exclusive interview, Assaf highlighted some of the major flaws within the insurance industry that are ready to be disrupted, the four ways to come up with a startup idea, why you need to go on a cofounder honeymoon before you get started, and many more topics.

Consultants vs. Entrepreneurs

Assaf was born in Israel, graduated from law school, studied business at the University of Chicago, and has worked at Intel Capital on its investment team.

Yet, he never did finish his term because he was already on the road to entrepreneurship at that point.

The first stop on his path to entrepreneurship was as a Senior Associate at McKinsey, where he built an amazing network. I've met so many founders that have come from McKinsey. Many of them have been so widely successful.

There were two real triggers that appear to have tipped Wand into entrepreneurship. The first was his realization that he was more passionate about defining and fixing problems, as entrepreneurs do daily than consulting for other companies.

Many consultants enjoy handing off well-defined solutions to others to execute. Entrepreneurs have a bug,  they just want to fix something and jump right in it to make it happen. The solution doesn't need to be 100% done for them to make the leap.

The second is that, as one of four boys in his household growing up, he knew he needed to pave his own path to make his mark. So he worked and studied tirelessly, to develop his own business.

Finding Startup Business Ideas

Assaf ultimately went back to Israel and co-founded two companies. One company, Foris Telecom, became the largest multi-tenant cellular tower business in India. They owned 11,000, 60-foot tall towers. Then they went to Mozambique, Uganda, and Tanzania and discovered growth in these countries as well.

Sabi was his most recent startup prior to Hippo Insurance. Sabi is a Japanese term meaning beauty in aging. Having patina and passing of time creates beauty and generates something with more character rather than something new. Just as a five-year-old oak hardwood floor is nicer than a new one because that shows the characteristics of it.

Sabi focused on bringing new designer products to Baby Boomers who hold most of the wealth, income and buying power in the U.S., but haven’t been well served by brands. Sabi grew to over $10 million in sales and was profitable before it was acquired.

Though having achieved several modest business exits Assaf Wand says “there's no bigger curse for an entrepreneur to build a company that gets to break-even at last, and is underfunded. It's just a massive curse. You can't make any big moves.” It takes the fun out of it.

Then, in 2015, Assaf co-founded  Hippo Insurance to offer intuitive and proactive home insurance by taking a smarter, tech-driven approach.

Their Seed round was $3 million. As of their Series C round in 2018, they had raised around $109 million. Investors include Lennar Corporation, GGV Capital, Felicis Ventures, Comcast Ventures, Munich Re Ventures, Aquiline Technology Growth, Abstract Ventures, Sinai Ventures, Fifth Wall and Propel Venture Partners. 

Hippo Insurance has mastered storytelling in order to be able to raise this kind of capital from some of the top tier investors. This is, in essence, being able to capture 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) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

Furthermore, Hippo Insurance has an average NPS score of 80, north of 100 employees, offices in Austin and Mountain View, have tens of thousands of customers and is growing by 25% per month.

Tips For Creating Startups

Today, Assaf  sees four ways that entrepreneurs can start a venture:

1. Expertise - see a problem in an  industry, and do it better

2. Consumer Problem Solving - create a solution to a pet peeve, pain or gap in markets you personally experience out there

3. Invention Driven - find a market for a new technology you’ve already created

4. Research Driven - dive into the data to find overlooked problems that can be solved and offer great scale and business opportunity

Assaf is a fan of the latter.

Cofounder Honeymoons

After several businesses, Assaf decided he had a specific need for his next startup - a strong co-founder.

Entrepreneurship is a roller coaster, you have amazing days and terrible days. Maybe in the morning, you think you are on top of the world, and then by the evening, you think the company is going to go down the toilet. You might go and meet an investor, and he says it's the best thing he's ever seen. On the same day, you can see someone that says it's the dumbest thing he's ever seen.

If you're by yourself, you are absorbing all of this by yourself. If you have a co-founder, then you have someone to mitigate it, as long as you found the right co-founder.

Assaf tackled this critical part of founding his latest venture by taking a month or two to ‘honeymoon’ with his chosen co-founder. He says they took a lot of walks together, went for a night out several times and truly got to know each other before they dug into work.

In terms of checking for alignment, he points to the personal and corporate culture issues that can make or break you later.

Such as:

  • Are you both thinking at the same scale in terms of dollars and an exit?
  • What lifestyles do you aspire to?
  • What hours do you plan to work?
  • How do you do work-life balance?
  • How do you view compensation for your employees?

If You’re Going to Launch a Business…

The one most important piece of advice Assaf says he would share with his younger self is to solve the biggest problem you can. There's no use in sitting down to solve incremental small problems. If you're committing your life to something, which is what entrepreneurship is, commit it to something big.


  • Strategies to raise financing
  • The process of recruiting the key team members
  • Scaling hyper-growth companies
  • How to find big ideas in big markets
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