Founder Friday is a content series from SuperAngel.Fund that highlights companies across our portfolio and the inspiring founders behind them.
Insurance is one of the largest line items for many businesses, yet most founders only realize what their policy doesnât cover when something goes wrong.
In our 58th edition, we are featuring JD Ross and Max Brenner, co-founders of With Coverage, an AI-enabled risk management and insurance platform helping businesses save money, improve coverage and proactively manage risk.
JD is a repeat founder who previously co-founded Opendoor, the real estate technology company that went public in 2021.
Max was part of the founding team at Compound, a technology-driven wealth management platform that now manages $1B+ in assets.
Today, most companies still rely on traditional insurance brokers and manage policies through emails, PDFs, and outdated systems.
As a result, many businesses:
⢠overpay for insurance
⢠have gaps in coverage
⢠lack visibility into their policies
⢠and donât have a dedicated risk management team
Enter With Coverage.
Instead of operating like a traditional broker, With Coverage combines an expert advisory team with modern software and AI to help companies better understand, optimize, and manage risk.
The platform centralizes policies, claims, certificates, and compliance in one place while proactively monitoring a companyâs operations to ensure the right coverage at the right time.
Unlike traditional brokers who are compensated through commissions, With Coverage operates on a flat-fee model, creating better alignment with customers and helping businesses save money while improving coverage.
Since launching in 2023, With Coverage has grown to support 700+ customers, including GoPuff, Bombas, Caraway, Windmill, Popsmith, Lalo, Hungryroot, Blank Street, Salt & Straw, Eight Sleep, and Chomps.
The company also recently announced a $42M Series B led by Sequoia, Khosla Ventures & Crystal Venture Partners, further validating its vision to modernize commercial insurance and risk management.
Want a complimentary insurance audit? Reply to this email and Iâll connect you with their team. Itâs free, wonât notify your existing broker, and could uncover meaningful savings or gaps in coverage.
See what JD and Max have to say in this weekâs Founder Q&A đ
Describe your company in 5 words or less?
JD: Replace your crappy insurance broker.
Max: Modern Risk Management Solution.
What was your primary motivation for starting your business?
JD: Every year I had to handle insurance at Opendoor, and it sucked so much that I knew we could build an amazing business by just being better.
Max: Attack a backwards and misaligned insurance industry where businesses consistently get overcharged, are mis-covered, and left with a poor and opaque experience. Mission is to provide a solution that actually puts businesses first, delivers substantial value, and leads with transparency.
What new product/feature are you most excited about and why?
JD: I love AI for how it makes our risk management offering superhuman, not just automation for cost savings.
Max: Claims Operating System. Weâve recruited top insurance attorneys to own handling claims for our clients, while pairing them with a claims management platform to identify repetitive problems and implement proactive solutions to better protect businesses.
What piece of advice would you give an entrepreneur starting a business today?
JD: Everything is now open for competition in a way it hasnât been in 10 years. Lean in hard to whatâs possible now that wasnât possible last year, and then extrapolate that further into the future.
Max: Obsess over the actual value you can deliver your end customer. People are exceptionally busy and your product must fundamentally be worth their time.
What do you love to do in your free time?
JD: I live in Austin, Texas now, which is basically the âhosting other peopleâ capital of the world. Come visit!
Max: Go for runs!
What is the most interesting place youâve visited recently and why?
JD: The OB/GYN office, nothing like seeing your baby growing.
Max: Japan. The cultural and societal contrasts are incredible and it truly feels like a different world.
What is your favorite app or tool in your work life and in your personal life?
JD: Codex and Claude -- everything else would be lying for cool points.
Max: Whispr - Voice to text tool.
What do you want to be when you grow up (besides a successful founder)? đ
JD: A great father and husband, a leader for the next generation, a good friend to many, and someone who leaves things better than I found them, over and over, ad infinitum.
Max: A great dad and husband? Ha! Work wise though I just love building things that make people happy.
What do you believe is the most important skill or attribute of a successful founder?
JD: Successful founders know why theyâre doing it. I think itâs incredibly important. Some people do it for money, for power, for legacy, or for love of the game. But if you donât know why youâre doing it, itâs very easy to burn out. Everything takes a lot longer than you think itâs going to take, but it also happens much faster than you think itâs going to happen. âThe days are long but the decades are short.â
Max: Relentlessness, while maintaining your kindness. People want to work with people they get along with, but you simply must be relentless in every part of the business.
Know a founder building something exceptional?
Reply to this email â Iâm always looking to meet great entrepreneurs.
SuperAngel.Fund is an early-stage venture capital fund led by Ben Zises that invests in Consumer, PropTech, & Future of Work đ.
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very interesting! the decades are short is going on the wall. congrats on the series B đĄď¸