My guest today is Assaf Wand, CEO, and co-founder of Hippo, a homeowner insurance startup founded in 2015. In March 2021, Hippo announced a SPAC merger, valuing the business at over $5bn. In our discussion, we cover how Hippo approached innovation in the highly regulated insurance industry, unique strategies for building brand trust, and how direct relationships with homeowners has opened up Hippo's business model to a wide range of opportunities. I was excited to speak with Assaf, given his experience as a serial entrepreneur, and he did not disappoint. Please enjoy my conversation with Assaf Wand.   For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience.   See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad, to help them grow their business. For a free trial, check out klaviyo.com/founders. ----- This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick." ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.   Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:02:44] - [First question] - His philosophy on business [00:04:04] - His first experience in entrepreneurship [00:05:03] - Lawyers vs entrepreneurs [00:07:03] - Major lessons taking risk in entrepreneurship [00:11:14] - Importance of speed in business [00:15:02] - Increasing urgency into the business as a leader [00:18:59] - What the insurance sector was like at the start of Hippo [00:24:49] - Steps he took to bootstrap trust [00:27:03] - Convincing partners [00:29:04] - Building the products and distribution [00:32:49] - Thoughts on innovators dilemma [00:35:00] - Flaws within the insurance industry [00:34:57] - Vision for the firm  [00:37:44] - Importance of culture in company building [00:41:19] - Storytelling as an essential piece of company building [00:41:50] - Building and managing a roadmap [00:43:19] - What does it mean to respect the customer [00:46:11] - Defensibility of the insurance industry [00:49:34] - Rewards of the trench warfare of entrepreneurship [00:53:33] - The feeling of getting wealthy  [00:55:29] - Kindest thing anyone has done for him