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Don’t Drive Off the Cliff: Use Your Cash to Your Advantage
Spencer Rascoff
andSpencer Rascoff serves as executive chairman of dot.LA. He is an entrepreneur and company leader who co-founded Zillow, Hotwire, dot.LA, Pacaso and Supernova, and who served as Zillow's CEO for a decade. During Spencer's time as CEO, Zillow won dozens of "best places to work" awards as it grew to over 4,500 employees, $3 billion in revenue, and $10 billion in market capitalization. Prior to Zillow, Spencer co-founded and was VP Corporate Development of Hotwire, which was sold to Expedia for $685 million in 2003. Through his startup studio and venture capital firm, 75 & Sunny, Spencer is an active angel investor in over 100 companies and is incubating several more.
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.
What’s the best way to land a plane on a short runway? Maintain control of your descent. The same logic holds for early- to mid-stage startups that are facing harsh financial conditions in 2023. Research from the end of last year found that 81% of early stage start-ups have less than 12 months of runway left. Yikes. Pair that with the current post-SVB venture investment freeze, and it paints a stark picture of what’s ahead.
A huge number of companies are going to be scrambling to find the emergency exit this year, as macro conditions make growth more challenging, and a dearth of venture capital means you need to move more quickly than ever.
If you’ve been grinding on your startup for years and haven’t found product/market fit, you have a critical decision to make now that capital is hard to come by.
You can keep doing what you’ve been doing, pivoting and hoping to find product/market fit. Eventually you’ll need a new source of capital to keep the lights on or a strategic acquirer when you’re at the end of your runway. You could also shut down the company and return cash to your shareholders. There is another option, though. You can flip your mindset and think like an investor to give yourself a more graceful landing.
Imagine, for example, a Series B stage startup with $20 million of cash, but burning $2 million a month. The company has 10 months of runway, is not likely to be able to raise a Series C, and does not yet have a path to profitability with its current business model. Instead of continuing with the current path and driving off the cliff when the 10 months are up, the company might consider cutting burn to almost zero, and sitting with its $20 million of cash.
In this hypothetical scenario, the startup could then try to find another company to merge with, providing its intellectual property, its user base, whatever team members remain, and most importantly its cash, as consideration (and leverage) in the merger. The $20 million of cash is something other companies want desperately in today’s market. Rather than driving off a cliff into a complete winddown or a small acquihire, this company could end up owning 25% of some other company, providing a clear path forward and a real chance at redefined success.
If you find resonance in this cautionary tale, remember: there are a lot of great potential acquirers out there who have found product/market fit and are scaling rapidly, but still can’t raise a venture round in today’s economic climate. These companies are looking for cash wherever they can find it. Said another way, they might have product/market fit but not enough cash, and you have cash but no product/market fit. Seems like a decent marriage, right?
If you’re a founder with cash on your balance sheet but no path forward, you have a unique opportunity to think of yourself as a venture capitalist and “invest” your company’s cash and equity into a new business.
So how do you do this? The key is to move fast and preserve your cash.
- Bring in the board. Have a frank discussion with your board and lead investors to decide if it’s time to call it quits. Most investors have seen a number of companies wind down or go through M&A exits, so they can be a great sounding board as you chart a path forward. They can also be great leads for potential acquirers and facilitate introductions.
- Slim down. In order to preserve your greatest asset—your cash—you unfortunately need to reduce burn everywhere you can including marketing, software spend, and headcount. Ideally, your ongoing costs should be minimal.
- Make a list. Think of all the companies in your space who could see acquiring your company as a good strategic move. Who do you respect most in your industry? Are they in a position to grow, and could this move turbocharge that growth? Who might benefit from the expertise on your team?
- Start the conversation. Once you’ve brainstormed, mine your contacts for warm intros and begin talking about your collective options. The M&A process can take a long time, so the sooner you get moving, the better.
- Negotiate terms and make your decision. Once you nail down the options, it’s up to you to decide whether or not a deal is the right move. Hopefully you can work with your acquirer and your investor base to find a good outcome for everyone involved.
If your startup is one of the many with cash in the bank but without a clear path to a next financing round, don’t panic. Now could be the chance to reimagine your best case scenario—invest your cash to find a new home for your company.
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Spencer Rascoff
Spencer Rascoff serves as executive chairman of dot.LA. He is an entrepreneur and company leader who co-founded Zillow, Hotwire, dot.LA, Pacaso and Supernova, and who served as Zillow's CEO for a decade. During Spencer's time as CEO, Zillow won dozens of "best places to work" awards as it grew to over 4,500 employees, $3 billion in revenue, and $10 billion in market capitalization. Prior to Zillow, Spencer co-founded and was VP Corporate Development of Hotwire, which was sold to Expedia for $685 million in 2003. Through his startup studio and venture capital firm, 75 & Sunny, Spencer is an active angel investor in over 100 companies and is incubating several more.
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.
https://twitter.com/spencerrascoff
https://www.linkedin.com/in/spencerrascoff/
admin@dot.la
More Screen Time? OK Play Says It's a Kids App Parents Won't Feel Guilty About
07:10 AM | September 03, 2020
Mr. Rogers made the boob tube acceptable television for a generation of kids and parents who had previously seen the small screen as antithetical to learning. Chris Ovitz wants do the same for his new mobile app OK Play, another in a recent blitz of edutainment products for children.
But this one, Ovitz said he has a twist: It's also made for parents. OK Play asks them to put their phones down and play with their young children.
"The way Mr. Rogers used the TV to reach so many families and talk about emotions — especially the hard ones — I think we can do something similar with the mobile device," said Ovitz, a founder and president of OK Play. "We can use that to create more connection between parents and children."
The company, which has already raised $11 million, launched its signature product on Thursday. It's backed by Obvious Ventures, Forerunner Ventures, Greycroft, but also the venture arms of the companies behind Sesame Street and Lego.
And if that sounds like a lot of cash for an app, it is. Ovitz, an entrepreneur who co-founded WorkPop and Viddy, said what he is actually creating is "a media company."
If his name sounds familiar it's because Ovitz is the son of the former Disney president and powerhouse behind CAA, Michael Ovitz, who also is an investor in the company. Ovitz grew up watching his powerful father create blockbusters and saw how they can stimulate the popular imagination and catapult an already successful company further.
The younger Ovitz is now the father of a four-year-old and said he had once carefully restricted his own son's screen time. But, he said, he wants to use the power of storytelling to draw in children. His vision was inspired by the documentary on Mr. Rogers, "Won't You Be My Neighbor."
"My first phone call was to JJ, who's the biggest empath," Ovitz said. OK Company CEO JJ Aguhob was a product and design consultant for Headspace and Musical.ly (now owned by TikTok's parent company ByteDance). "I was like, 'You got to watch'."


The two began plotting out their path and brought on several other co-founders including Colleen Russo Johnson, a developmental psychologist with an expertise in children's media and technology who is the company's chief scientist. Much of her work showed that screen time wasn't always bad, if parents helped guide children.
What the team designed was an interactive application populated by a cast of recurring characters: Mapa and her friends.
The characters are each designed for a different type of play. Jicama, the artist, is all things creative. Kim and Tim, workout enthusiasts, are all things active.
A premium version of the app costs $9.99 a month or $59.99 a year.
Each day, parents will find a fresh batch of activities to engage in with their kids. While doing so, they are encouraged to create special "moments," so kids can record, for example, how they feel one day - angry or sad.
Those 'memories' can then later be tapped and used to motivate parents to keep using the application. Another section of the app guides parents through the developmental framework.
"Our goal is to get kids and parents playing together, spending quality time and, through that, growing their social and emotional skills, which are extremely important for young children to focus on," said Russo Johnson.

Founding team JJ Aguhob, Chris Ovtiz, Dr. Colleen Russo Johnson, Ken Chung and Travis Chen
Originally, OK Company planned to launch their app later this year, but the pandemic left so many families stuck at home searching for child activities that it accelerated the timeline for their launch.
"We really want to try and help strip away the stress and pressures on parents, remind them that it's okay to just be wherever they are," she said.
The company will compete in an increasingly crowded multi-billion-dollar edutainment marketplace, but their ambitions are to transcend it.
"I think the overarching dream for us is to build that once-in-a-generation children's entertainment and technology company, but we can't get there until we really start to build this," said OK Company CEO Aguhob.
"We are at the starting line," he said, noting there is room to grow eventually adding books, toys and other physical merchandise that traditional media franchises have used to expand their reach.
"We're not just going to make traditional entertainment because it's the thing that you do," he said "We're going to create a new interactive experience that brings families together. And from that, the media is going to look different."
Do you have a story that needs to be told? My DMs are open on Twitter @racheluranga. You can also email me.
**An earlier version misidentified Michael Ovitz's title.
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Rachel Uranga
Rachel Uranga is dot.LA's Managing Editor, News. She is a former Mexico-based market correspondent at Reuters and has worked for several Southern California news outlets, including the Los Angeles Business Journal and the Los Angeles Daily News. She has covered everything from IPOs to immigration. Uranga is a graduate of the Columbia School of Journalism and California State University Northridge. A Los Angeles native, she lives with her husband, son and their felines.
https://twitter.com/racheluranga
rachel@dot.la
Cap Tables to Costumes: Whatnot’s Mega Round and Your LA Weekend Plan 🎃
10:39 AM | October 31, 2025
🔦 Spotlight
Happy Friday Los Angeles!
Live shopping’s LA moment
Whatnot, the LA born marketplace for live auctions, raised $225 million at an $11.5 billion valuation. The round was co led by DST Global and CapitalG, with Sequoia, Alkeon, a16z, Greycroft, BOND, and others participating. The company says the money goes to international expansion, trust and safety, and seller tools - fuel for a category that has moved from “Is this a fad?” to “How big does this get in the West?”
Why it matters
If that valuation sounds sudden, you’re not imagining it. Whatnot’s last raise in January valued the company around $5 billion. Less than 10 months later, the number has more than doubled, tracking a year of surging GMV and a social commerce flywheel spinning across TikTok Shop, YouTube, and Amazon. For LA, it’s a marquee bet on the creator commerce stack we do best: community, content, and culture that converts
The bigger picture
The implications go well beyond trading cards. Live, personality led storefronts are evolving from hobby to underwritable small business. If Whatnot uses this cash to keep fraud low and throughput high, we could see an LA export take root globally, not just as an app category but as a job category. That is a storyline to watch into Q4 and beyond.
From cap tables to costumes: Halloween in LA 🎃
You’ve earned some offline fun. Heading into Halloween weekend (Oct. 31–Nov. 2), LAist’s guide has a little of everything: neighborhood Día de los Muertos celebrations (from the Canoga Park family festival to an ofrenda for pets at Annenberg PetSpace in Playa Vista), the Frogtown Arts weekend along the LA River, plus plenty of screenings and concerts across town. Bookmark the list, pick your neighborhood, and maybe swap “add to cart” for “add to calendar.”
Send tips, sightings, and spooky term sheets our way. Venture deals for LA companies, funds, and acquisitions are below.
🤝 Venture Deals
LA Companies
- Bryan Johnson’s longevity startup Blueprint raised $60M from a celebrity heavy group of backers including Kim Kardashian, Naval Ravikant, Alex Hormozi, Ari Emanuel, and the Winklevoss twins to turn Johnson’s personal Blueprint regimen into a broader consumer platform. The company says the funding will help package diagnostics, biomarker tracking, prescriptions, nutrition, and other longevity services into an accessible offering. The round underscores mainstream interest in data driven wellness despite past questions about Blueprint’s trajectory. - learn more
- Rarity PBC raised $4.6M in seed financing to advance a one-time, autologous blood-stem-cell gene therapy for ADA-SCID (“bubble baby” disease) that it has licensed from UCLA researcher Dr. Donald Kohn. The round, led by biotech investor Steve Oliveira (Nemean Asset Management), will support manufacturing and steps toward commercial readiness. - learn more
- Fruitist raised $150M led by a vehicle managed by J.P. Morgan Asset Management, with participation from Aliment Capital and Ray Dalio’s family office. The LA-based superfruit brand says the funding will fuel crop expansion, cold storage, and automation as it scales distribution to 12,500+ stores and targets continued growth following roughly $400M in trailing sales. - learn more
- Homecourt, the Los Angeles based luxury home and personal fragrance brand founded by Courteney Cox, raised an $8M Series A led by CULT Capital. The company says the funding will fuel brand marketing, team hires, and infrastructure as it expands beyond DTC into 300+ retail doors including Nordstrom, Bluemercury, and Revolve. Homecourt has broadened from home care into body and laundry collections since launching in 2022. - learn more
LA Venture Funds
- Aliavia Ventures participated in Human Health’s $8.5M raise, joining LocalGlobe, Airtree, Skip Capital and Scale Investors to back the precision health platform from former Canva product leaders Georgia Vidler and Kate Lambridis. The funding will support international expansion, deepen product intelligence in areas like women’s health, respiratory and pain, and scale Human Evidence for patient driven research; Human Health reports more than 200,000 users and 20 million logged health actions to date. - learn more
- Riot Ventures participated in EnduroSat’s $104M funding round, alongside Google Ventures, Lux Capital, the European Innovation Council Fund, and Shrug Capital. The Sofia based satellite manufacturer says the capital will scale production of its ESPA class (200 to 500 kg) modular satellite buses, targeting capacity of up to two satellites per day at a new 188,340 square foot Space Center so constellation customers can get to orbit faster. The raise is EnduroSat’s second this year and follows a €43 million round in May. - learn more
- Rocana Venture Partners participated in Recess’s $30M Series B, which was led by CAVU Consumer Partners and included Midnight Ventures, Torch Capital, Doehler Ventures, KAS Venture Partners, Vanquish, and Craig Kallman. The relaxation-beverage company will use the capital to grow its team, expand retail distribution, and ramp marketing, and it also named former Nutrabolt executive Kyle Thomas as President and Co-CEO to help scale the brand. Recess says it now sells in more than 15,000 U.S. stores, positioning it to capitalize on demand for functional relaxation and alcohol-alternative drinks. - learn more
- Terasaki Institute participated in iOrganBio’s $2M launch financing, joining First Star Ventures (lead), IndieBio, Cape Fear BioCapital, 2ndF, and Alix Ventures. The Chapel Hill based startup unveiled CellForge, an AI powered cell-manufacturing platform that pairs predictive models with high throughput control to engineer reproducible human cells and organoids for drug discovery and cell therapies. The funds support product development and early deployments. - learn more
- Fox Sports made a strategic investment in Shadow Lion, the creative agency and IP studio co-founded by Tom Brady, forming a partnership to develop talent-led originals, digital content, long-form projects, and marquee live events. The deal includes a new Los Angeles hub for Shadow Lion on the Fox lot, with early tentpoles including a University of Michigan football docuseries from executive producers Brady and Jim Harbaugh and collaboration on the Fanatics Flag Football Classic. - learn more
- EB Medical Research Foundation participated in Eliksa Therapeutics’ funding to advance ELK-003, a biological eye drop for ocular complications in epidermolysis bullosa. The round, led by DEBRA Research with support from Cure EB, the Abe Fund, and EB Research Partnership, backs an ongoing pilot study with 18 patients enrolled and no drug-related side effects reported among the first eight who completed treatment. - learn more
- Patron and HartBeat Ventures participated in Sweatpals’ $12M seed round alongside a16z speedrun, backing the community fitness platform as it expands its “daylife” model of IRL wellness events. The funding will support product and market expansion for hosts and gyms using Sweatpals for discovery, ticketing, memberships, and marketing. Business Insider reports the startup now reaches over 1 million monthly users and is growing into new U.S. cities. - learn more
- UP.Partners participated in Lula Commerce’s $8M Series A, led by SEMCAP AI with Rich Products Ventures, GO PA Fund, NZVC, Green Circle Foodtech Ventures, and Outlander VC also joining. The Philadelphia company, active with more than 2,000 retailers, offers an AI powered digital commerce suite for convenience stores covering order ahead, pickup, delivery, and back office tools, and says the round brings total funding to over $16M to meet rising demand. - learn more
- Navitas Capital led WorkHero’s $5M seed to scale its AI powered back office platform for small HVAC contractors, with Workshop Ventures, York IE, and strategic angels also participating. WorkHero combines agentic AI with human account managers to handle invoicing, permits, rebates, warranty registrations, and pricebooks so owners spend less time on admin. The funding will expand engineering and product and add new services such as call answering and bookkeeping. - learn more
LA Exits
- DMI was acquired by Stingray, adding about 8,500 U.S. retail locations to Stingray’s in-store audio advertising network and bringing its total footprint to roughly 33,500 sites. The deal cements Stingray’s leadership in pharmacy retail audio across the two largest chains and brings DMI’s creative services, including cinema advertising and brand marketing, under its umbrella, with CEO Tena Clark staying on to help integrate and expand the offering. - learn more
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