⛈ Sensible: The White Knight of Weather

Wil Chockley
WIl Chockley is a partner at 75 & Sunny, where he evaluates potential investment opportunities across sectors and works with founders to build their strategy and execute on their vision.
⛈ Sensible: The White Knight of Weather
https://www.sensibleweather.com/

Picture this: you’ve saved up for months for your dream beach vacation. You’ve cut out restaurant dinners, morning coffees, and those concert tickets you really wanted. You bought your flights and made your hotel reservation. You finally step off the plane in your tropical paradise, only to see that the weather forecast has changed while you were in flight. It’s now supposed to rain for the next 3 days straight…

Source: Peter Cade, The Times of London

Every year, this happens to thousands if not millions of travelers, and, until recently, there was nothing you could do except grit your teeth and “enjoy” sitting in your hotel room reading your mystery novel while your hard earned money evaporates.

Nick Cavanaugh has made it his life’s mission to change that. His company, Sensible, offers the world’s first “Weather Guarantee.” Unfortunately, Sensible can’t literally guarantee the weather will be perfect for your next vacation, but they can insure your trip, such that you get paid a refund if the weather ruins your getaway. Very soon, if it rains on your beach vacation, you can breathe easy because the money you worked so hard to save will go right back into your bank account, and you get a free or discounted vacation to boot.

⛈️ Pre-Sensible

The Sensible story starts in one of the most notoriously rainy places in America: Seattle. Nick Cavanaugh was an outdoorsy kid who loved to ski. Fortunately for him, the Pacific Northwest is full of beautiful ski mountains, but unfortunately for him, the temperatures at many of these mountains hover right around freezing, so rainy skiing was just a fact of life for Nick. Year after year, Nick’s ski trips got rained out, or he skied and got rained on.

Eventually Nick moved out of Seattle to attend the University of Pennsylvania in Philadelphia, where he studied Engineering, with a minor in Environmental Science. While a student at Penn, he came back to the west coast to intern at the world-renowned UC San Diego Scripps Institution of Oceanography where he found the perfect marriage of his passions for math and the outdoors. He was hooked.

After graduation in 2010, Nick returned to the Scripps Institute and four years later completed his masters and PhD in Atmospheric Dynamics and Physics. Nick then spent another two years as a postdoctoral fellow at the Lawrence Berkeley Laboratory (named for Ernest Lawrence, inventor of the cyclotron and J. Robert Oppenheimer’s frenemy in the movie). After 10 years in academia with a hyper-specialized degree and set of skills, Nick had a couple options - he could remain in academia and research, he could work in catastrophe insurance, or he could explore an emerging niche segment of Wall Street, weather-focused hedge funds.

Given Nick hadn’t really made money in his adult life, the hedge fund angle seemed pretty interesting, and he moved to New York to join a fund called Cumulus. At Cumulus, he was focused on predicting weather patterns and inferring their effect on energy and commodity prices. During Nick’s time at Cumulus, the scrappy little fund was acquired by mega-fund Citadel, and Nick looked for the exits.

After leaving Citadel, Nick moved to Los Angeles to get back to the sunny weather, surfing, and outdoorsy culture of Southern California while he thought of what to do next. As he was brainstorming, his mind kept coming back to those rainy childhood ski trips. He was one of probably 25 people in the world with deep experience in both advanced weather prediction and complex financial products, so he decided that he just might be the right person to solve his childhood problem.

☀️ Sensible

To make this happen, Nick needed some initial funding. In 2021, he connected with local LA VCs Dustin Rosen from Wonder Ventures and Josh Diamond from Walkabout Ventures who came together to lead Sensible’s Seed Round and get the business off the ground.

Since then, Nick and team have been building the fastest and most accurate local weather prediction engine in the world. Today, Sensible is constantly ingesting hundreds of terabytes of weather data from NOAA (National Oceanic and Atmospheric Administration) and the ECMWF (European Centre for Medium-Range Weather Forecasts). The craziest aspect of Sensible’s product is not that they are able to ingest the data, but rather that they are able to generate quotes based on a completely personalized, local prediction in less than half a second. Not only can they spit out an individual quote in half a second, but they can spit out more than 60,000 quotes per second across their platform.

So how do you get one of these Sensible Weather Guarantees?

Sensible’s go-to-market strategy thus far has been B2B2C, where the team partners with end merchants (e.g., ski resort Mt. Baldy) as well as infrastructure providers (e.g., ticketing provider Catalate). As a consumer, you find Sensible in the checkout flow of your booking experience, similar to how you find travel insurance in your airline ticket checkout.

For example, when I went to book through Sensible partner Aquarius Boat Rentals, I was shown this screen:

As you can see, adding Sensible’s Weather Guarantee is pretty darn simple - just click yes in the dropdown, and it’s automatically added to your purchase price. Pricing of the policy is algorithmically determined based on the likelihood of rain and a multitude of other complicated factors. Depending on the policy you pay for, you can get a full or partial refund paid out by Sensible’s reinsurance partner (importantly, not the merchant or channel partner).

According to Nick, merchants can benefit from Sensible in two ways: 1. Buyers are more likely to buy if they have peace of mind knowing they will be reimbursed for inclement weather 2. Merchants can mark up the cost of the guarantee and actually make additional revenue from selling the policies.

This all seems like the legendary Michael Scott win-win-win.

Luxurious Second Home Ownership without the Headache: How Pacaso is Changing the Landscape of Real Estate

🔦 Spotlight

Pacaso addresses the pain points of second home ownership, offering a luxurious, flexible, and financially sound alternative to traditional second homes and ultra-luxury hotels. Co-founded in 2020 by entrepreneur Austin Allison and former Zillow executive and prominent LA tech figure Spencer Rascoff, Pacaso, an unicorn startup, has redefined vacation home ownership with its unique co-ownership model. Rascoff's contributions to the LA tech scene extend beyond real estate; he also founded 75 & Sunny, an LA-based startup studio and venture fund, and co-founded dot.LA, an LA tech news and events company.

LA residents adore Pacaso for its lush vacation destinations that also make for smart investments. Pacaso offers everything from serene weekend getaways in Aspen to sophisticated escapes in Paris. Each residence, valued between $200k to over $2M for 1/8th, boasts meticulous design, high-end furnishings, and premium amenities. Unlike traditional second home ownership, which involves high costs, maintenance, and underutilization, or ultra-luxury hotels, which lack the personal touch and investment potential, Pacaso's co-ownership model offers a superior solution. Co-owners enjoy the benefits of a high-end vacation home without the full financial burden and hassle of sole ownership, making it a smarter and more flexible choice for discerning buyers.


Image Source: Pacaso

Cabo, Mexico

$822,000 (1/8th ownership)

5 bds. l 5 ba. l 4,969 sq ft

View Here


Image Source: Pacaso

Paris, France

$600,000 (1/8th ownership)

2 bds. l 2.5 ba. l 1,410 sq ft

View Here


Image Source: Pacaso

Malibu, California

$750,000 (1/8th ownership)

3 bds. l 3 ba. l 1,880 sq ft

View Here


Image Source: Pacaso

Park City, Utah

$755,000 (1/8th ownership)

4 bds. l 4.5 ba. l 2,584 sq ft

View Here

Head to Pacaso to learn more about its innovative co-ownership model that addresses the common challenges of second home ownership!


🤝 Venture Deals

LA Companies

  • Oak Essentials, the natural skincare brand founded by Jenni Kayne, has raised an undisclosed amount in Series A Funding from Silas Capital and Unilever Ventures. This investment will drive the brand’s expansion, focusing on product development, boosting marketing efforts, and expanding distribution channels. - learn more
  • Playhouse MD, an upcoming children’s healthcare platform that incorporates play to enhance health outcomes, has raised $4M in funding, according to a recent SEC filing. - learn more
  • FluidLogic, a high-performance hydration system provider, raised $15M in a Series A Extension led by Solyco Capital to support product development and innovation for adventure sports and outdoor endurance categories, with consumer products launching in early 2025. - learn more
  • Reflect Orbital, which uses in-space reflectors to direct sunlight to solar farms and large-scale lighting applications after sunset, has raised $6.5M in seed funding led by Sequoia Capital. The funding will help the company develop production vehicles and expand its team as it builds space-based energy infrastructure. - learn more

LA Venture Funds
  • Smash Capital led a €20M Series B round into Vilnius-based Ovoko, an e-commerce platform for buying and selling used car parts across Europe, marking Smash Capital's first investment in Lithuania. The funds will support Ovoko's product development, market expansion, and team growth as it aims to dominate the European market for second-hand automotive components. - learn more
  • M13 led a $9M Series A Funding Round for Zenlytic, the world’s first self-serve business intelligence platform. - learn more



LA Exits

  • Continuum Global Solutions’ healthcare vertical has been acquired by Everise, a customer service management company, enhancing Everise’s capabilities in pharmacy benefit management and expanding its growth prospects in the healthcare sector. - learn more
  • Radical Semiconductor, a company specializing in processing-in-memory technology, has been acquired by BTQ Technologies, a leader in post-quantum cryptography. This acquisition strengthens BTQ’s ability to secure data in the post-quantum era by integrating Radical Semiconductor's advanced technology portfolio. - learn more

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🎧The Essential Podcast Playlist for Entrepreneurs, Founders, Tech Pros, and VCs

Podcasts offer a front-row seat into the minds of the most successful entrepreneurs, VCs, and industry thought leaders. Whether you're scaling your startup, raising capital, or simply staying ahead of the game, these shows deliver invaluable insights, actionable lessons, and fresh inspiration. And let’s be honest, if you’re stuck in LA traffic (again), what better way to kill time than by learning from the best? Here’s a roundup of our top podcasts for entrepreneurs, founders, tech professionals, and VCs, complete with why they’re a must-listen.

Image Source: Apple Podcasts

The a16z Podcast

  • What it discusses: Covering a broad spectrum of topics like AI, blockchain, healthcare, and fintech, the podcast features interviews with founders, VCs, and tech leaders shaping the future.
  • Why you should listen: Get access to cutting-edge insights from one of the world’s most influential VC firms, keeping you ahead of emerging trends.
  • Why it’s great for entrepreneurs, founders, and VCs: This podcast brings cutting-edge insights from one of the top VC firms. Entrepreneurs will learn about emerging technologies, while VCs can stay ahead of investment trends shaping the future of tech.

Listen on: Spotify |Apple Podcasts



Image Source: Apple Podcasts

Acquired Podcast

  • What it discusses: Acquired breaks down the stories behind major tech acquisitions, IPOs, and exits, dissecting the strategies and market dynamics involved.
  • Why you should listen: Gain deep insights into how tech giants build and sell, making it essential for anyone aiming to understand successful exits.
  • Why it’s great for entrepreneurs, founders, and VCs: Perfect for founders looking to scale or position themselves for acquisition. VCs will benefit from the deep dives into the playbooks of successful exits, offering valuable lessons on company growth and market positioning.

Listen on: Spotify |Apple Podcasts



Image Source: Apple Podcasts

The All-In Podcast

  • What it discusses: From venture capital and tech trends to politics and economics, this podcast delivers unfiltered, candid commentary from high-profile industry insiders.
  • Why you should listen: It’s a no-holds-barred discussion on major issues affecting the tech industry, providing you with insider insights into the conversations that shape Silicon Valley.
  • Why it’s great for entrepreneurs, founders, and VCs: The candid, unfiltered conversations give listeners a peek into the decision-making processes of some of the biggest names in tech and VC. Entrepreneurs can gain valuable market insights, while investors will appreciate the high-level strategy discussions.

Listen on:Spotify | Apple Podcasts



Image Source: Apple Podcasts

BG2 Podcast

  • What it discusses: BG2 takes you through macroeconomic trends, the tech market, venture capital insights, and cutting-edge technologies like AI. It’s a high-level conversation on tech investing.
  • Why you should listen: Brad and Bill’s deep experience in tech investing, combined with their straightforward, no-nonsense style, makes this a must-listen for tech insiders.
  • Why it’s great for entrepreneurs, founders, and VCs: Get insider-level insights into the macro trends driving tech investments. Founders will learn how to navigate these trends, while VCs can better understand the shifting forces in the venture world.

Listen on: Spotify | Apple Podcasts



Image Source: Apple Podcasts

Crucible Moments Podcast

  • What it discusses: The podcast dives into the pivotal, career-defining moments of top leaders and entrepreneurs. Guests share personal stories of resilience, growth, and how they overcame adversity.
  • Why you should listen: It’s packed with inspirational stories of grit and perseverance, offering lessons that apply to both life and business.
  • Why it’s great for entrepreneurs, founders, and VCs: The podcast’s focus on personal and professional resilience makes it especially valuable for entrepreneurs who need inspiration during tough times, and VCs who want to understand how founders overcome adversity.

Listen on: Spotify | Apple Podcasts



Image Source: Apple Podcasts

Grit Podcast

  • What it discusses: In-depth interviews with founders, executives, and leaders who share stories of navigating challenges, building resilience, and finding success in tough times.
  • Why you should listen: If you want raw, real stories of leadership and determination, this podcast offers invaluable insights into what it takes to lead in business.
  • Why it’s great for entrepreneurs, founders, and VCs: The podcast’s focus on perseverance and leadership makes it a must-listen for founders facing challenges in their business. VCs will gain insights into the traits that make strong, resilient founders.

Listen on: Spotify | Apple Podcasts



Image Source: Apple Podcasts

The Twenty Minute VC

  • What it discusses: Featuring short, insightful interviews with top VCs and founders, this podcast covers topics ranging from securing funding to scaling startups.
  • Why you should listen: Perfect for busy professionals who want quick, actionable advice on navigating the venture capital world.
  • Why it’s great for entrepreneurs, founders, and VCs: For busy entrepreneurs, this podcast delivers quick, actionable advice on funding and scaling. VCs can stay connected to the latest trends through bite-sized interviews with industry leaders.

Listen on: Spotify |Apple Podcasts


These podcasts are packed with insights, inspiration, and actionable advice for anyone looking to grow, innovate, or level up. Whether you're building something new, looking for investment know-how, or just eager to learn from those who've been there, each show has something valuable to keep you moving forward on your journey.

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📱From Digital IDs to AI Feeds: Tech Giants Shake Up the Digital World

🔦 Spotlight

Happy Friday Los Angeles!

This week, two tech titans, Apple and Snapchat, announced groundbreaking updates that are poised to reshape the way we interact with our digital devices. From secure digital IDs to personalized AI feeds, these innovations are set to have a significant impact on our daily lives.

Apple's Digital Driver's License: A Game-Changer for LA Residents

Apple has taken a major step forward in digital identity with the integration of California driver's licenses and state IDs into Apple Wallet. This initiative, part of the state's mobile driver's license (mDL) program, offers a more convenient and secure way for LA residents to carry their identification. With encrypted data and NFC-enabled verification, users can now use their digital IDs at TSA checkpoints, select retailers, and even for age verification at bars and restaurants.

The mDL program not only simplifies travel and everyday transactions but also presents exciting opportunities for LA-based startups specializing in fintech, cybersecurity, and identity verification. As digital IDs become more widely adopted, these startups can innovate to create new applications and services that leverage this technology.


Image Source: Snap

Snapchat's AI-Powered Feed and Enhanced AR: A Personalized Experience

Snapchat is undergoing a major transformation with its most significant redesign in years, focusing on simplicity and personalization. The app now offers a more personalized experience, with an AI-driven "For You" feed that curates content tailored to individual preferences. Additionally, Snapchat has enhanced its augmented reality (AR) tools, opening up new possibilities for interactive experiences and creative expression.

LA's thriving tech ecosystem, particularly its startups focused on AI and AR, stands to benefit greatly from Snapchat's innovations. These updates provide opportunities for local developers to create complementary technologies and explore new partnerships within Snapchat's evolving platform.

Impact on LA's Tech Ecosystem

Both Apple's and Snapchat's updates underscore a growing trend toward personalization, security, and streamlined user experiences. LA's tech scene, with its vibrant startup community and strong focus on innovation, is well-positioned to capitalize on these shifts.

As digital experiences become more integrated into our daily lives, LA's startups can explore new frontiers in AI, AR, and secure mobile technologies. This wave of innovation is set to drive growth and collaboration within the local tech ecosystem, solidifying LA's reputation as a global hub for cutting-edge technology.


🤝 Venture Deals

LA Companies

  • PictorLabs, an AI-powered histopathology platform that enhances disease detection, has raised a $30M Series B led by Insight Partners. The company has now raised a total of $48.8 million. - learn more
  • Mellomanic, formerly We Are Giant, has raised a $6M Funding Round, bringing its total capital to $13.8M, to expand its platform and enhance its music experiences for artists and fans, backed by investors including Sterling Partners. - learn more

    LA Venture Funds

    • Mucker Capital participated in a $2.5M Seed Round for Tab Commerce, a fintech company providing financial management solutions to transform how restaurants handle their spending and optimize operational efficiency. - learn more
    • Finality Capital led a $3.2M Seed Round for RISE, a Gigagas Layer 2 blockchain platform designed to enhance scalability and reduce transaction costs. - learn more


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