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XHow to Startup: Mission Acquisition
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.
Numbers don’t lie, but often they don’t tell the whole story. If you look at the facts and figures alone, launching a startup seems like a daunting enterprise. It seems like a miracle anyone makes it out the other side.
- 90% of startups around the world fail.
- On average, it takes startups 2-3 years to turn a profit. (Venture funded startups take far longer.)
- Post-seed round, fewer than 10% of startups go on to successfully raise a Series A investment.
- Less than 1% of startups go public.
- A startup only has a .00006% chance of becoming a unicorn.
Ouch.
If your goal is to reach billion-dollar valuation and be publicly traded, the odds will never be in your favor. It does happen, of course, but it’s an exceedingly rare outcome for even the best startups. Holding on too tightly to that hypothetical can actually work against you, blinding you to the importance of planning for a different kind of exit.
It’s been said before, but it bears repeating—companies are bought, not sold. Better exits happen when someone sees the value your startup can bring to their business and is actively trying to purchase it, rather than you having to convince prospective buyers of what your services or products can bring to the table. In the latter scenario, your footing is much less secure and your odds of a successful transaction are inherently lower. You have much more power and are in a much better position when buyers are actively pursuing you.
Getting acquired may not feel like the fairy tale ending your startup deserves, but it’s more than just a back up plan—and it doesn’t happen by accident. Beginning to build the infrastructure today can give you much more control of what happens to your company in the future.
Here’s my advice to startup founders who want to be savvy about their acquisition strategy:
- Make a Buyer List: If your startup has successfully reached Series A or B funding, it’s time to put pen to paper and make a list of your top potential acquirers. Doing so does not indicate failure, just prudence. Who is in your space and could benefit from your company? What company would you like to be a part of? Who shares your mission? Questions like these can help guide you. Aim for having between 10 and 25 potential acquirers in mind.
- Make Connections: Now that you have your short list of companies, be intentional about reaching out and forging relationships with their leadership team. Shoot for the top—a CEO-level contact is ideal. Also consider speaking with people at Corporate Development, but don’t forget another key area of focus—the operating level.
Say, for example, you’re a rental software startup that serves the multifamily sector. Zillow would be a natural fit for your M&A list. Instead of just going after the Corp Dev contact, get to know the person at Zillow who runs the rental business. M&A deals need executive sponsors from the operating unit. Understanding what they do and how they do it is a big advantage when envisioning how your start up can fit into their ecosystem. - Make Those Connections Count: After you’ve connected with the right people at your potential acquirers, make sure you keep them in the loop. Every quarter or six months, reach out to them directly to keep them apprised of what’s going on in your business areas. Tell them what you’re working on. Share your big wins. Ask about potential business development partnerships. See how you might be able to sync up and compare notes.
If you go into these conversations in the name of collegial collaboration, you can form meaningful business relationships that can lead to the best possible outcome for both parties: your startup getting acquired and their company gaining new value.
We acquired 16 companies during my decade as CEO of Zillow. I estimate that the median length of time from the first time I met each of those 16 founders to when the acquisitions were completed was three years. It takes a long time to build relationships with strategic acquirers. Get started now.
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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.
https://twitter.com/spencerrascoff
https://www.linkedin.com/in/spencerrascoff/
admin@dot.la
GOAT Co-founder Eddy Lu On How His Sneaker Startup GOAT Achieved Unicorn Status
09:37 AM | May 19, 2023
Eddy Lu
With LA Tech week approaching, I had to pull one of my favorite Office Hours’ episodes spotlighting a unicorn ecommerce sneaker startup GOAT, when co-founder and CEO Eddy Lu talked about how he achieved success and shared his insight on when to know if it's time to pivot or quit.
Serial entrepreneur Lu and his co-founder Daishin Sugano are both L.A. natives and believe that the city of angels is where GOAT is meant to be.
“There is just no better place than L.A. to launch a consumer facing company because there's such a diversity of customers,” he said. “And it's not as homogenous as some other areas in terms of the experiences that people can bring.”
Prior to launching GOAT, Lu and Sugano worked together on a few other businesses that were mostly unsuccessful.
They raised a Series A of $6 million from Upfront Ventures for their first startup, Grub, with Us, after participating in Y Combinator’s program. But unfortunately, Lu said they came across too many friction points and needed to pivot.
”You really have to be honest with yourself,” he said. “So we tried to remove every single friction point from what we got from customer feedback and at that point, it still wasn't working. So we said, ‘It's really time to move on.’”
Shortly after, the two focused all of their energy into launching their sneaker marketplace GOAT at a time when the sneaker reseller market was booming. Lu said that at one Black Friday event, the team decided to discount the hottest sneakers of 2015 to retail prices ($200).
Local sneaker publications caught wind of this news and it blew up. Due to the overwhelming coverage, GOAT signed over 100,000 new users onto the platform a week before the shoe drop.
As exciting as this was for Lu and the business, the platform was not built to withstand that many individuals accessing it all at once.
“As you can imagine when 100,000 people try to access a non-skilled server on the same exact second, on the same exact day, chaos ensues,” he said. “So nothing worked on Black Friday and people were so mad at us. We had 1000s of customer service complaints, death threats on Instagram, it was just madness.”
But despite the user outrage they received, the situation was quickly rectified and a trusted advisor shared some advice: "at this stage in your company's life, it's better to be hated than unknown."
Lu said that while looking back at that day was so painful, he would have done it a thousand times over because “that was our true inflection point.”
“We literally did not look back from that point in time because while our consumers hated us at that moment,” he said, “they experienced the app and they started to understand our value proposition.”
To date, GOAT has over 30 million members, over 100,000 SKUs and over 2 million listings.
“It's because of that exact moment where people started to understand what we did so that they could just trust us,” Lu said.
dot.LA Reporter Decerry Donato contributed to this post.
Want to hear more episodes? Subscribe to Office Hours on Stitcher, Apple Podcasts, Spotify, iHeart Radio or wherever you get your podcasts.
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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.
https://twitter.com/spencerrascoff
https://www.linkedin.com/in/spencerrascoff/
admin@dot.la
Skyryse Raised $300M+ to Do What Most Startups Can’t
09:26 AM | February 06, 2026
🔦 Spotlight
Hello Los Angeles
LA just minted another aviation unicorn, and it is not because someone built a prettier helicopter demo. It's because Skyryse is trying to do the rarest thing in tech: turn software into something regulators will sign their name to, and that pilots will trust when conditions are at their worst.
El Segundo’s newest unicorn is simplifying the cockpit
Skyryse raised $300M+ in a Series C at a $1.15B valuation. The round was led by Autopilot Ventures and returning investor Fidelity Management & Research Company, with participation from Qatar Investment Authority, ArrowMark Partners, Atreides, BAM Elevate, Baron Capital Group, Durable Capital Partners, Positive Sum, Rokos (RCM Private Markets Fund), and Woodline Partners, among others.

The pitch is bold and deceptively simple. Skyryse is building a “universal operating system for flight,” SkyOS, designed to replace the cockpit’s maze of mechanical controls with a computer-driven system that makes routine flight easier and emergency situations more manageable. The bigger claim is standardization: if you can make the interface and controls feel consistent across aircraft, you reduce training friction, lower pilot workload, and create fewer opportunities for human error when the stakes spike.
The real work starts after the press release
Skyryse says the funding will be used to accelerate FAA certification and scale SkyOS across additional aircraft platforms, including the Black Hawk. That is the hard part, and also the part most startups never reach. Aviation is where software has to prove itself in edge cases, repeatedly, with zero tolerance for surprises, because “mostly works” is another way of saying “eventually fails.”
The bet hiding inside the headlines
If Skyryse clears certification and can port SkyOS across aircraft types the way software ports across devices, it could unlock a new category of safety automation for fleets that cannot afford downtime, confusion, or long training cycles. Emergency response, defense modernization, and industrial aviation are all markets where reliability is the product, and simplicity is the differentiator. In a world obsessed with shipping faster, Skyryse is playing a different game: getting permission to ship at all.
Keep scrolling for the latest LA venture rounds, fund news and acquisitions.
🤝 Venture Deals
LA Companies
- Accrual announced it has raised $75M in new funding led by General Catalyst, with participation from Go Global Ventures, Pruven Capital, Edward Jones Ventures, and a group of founders and industry executives. The company says the raise supports its official launch and continued buildout, alongside early partner firms, investors, and advisors. - learn more
- Morpheus Space secured a $15M strategic investment led by Alpine Space Ventures and the European Investment Fund, with continued support from existing investors, to fuel its next phase of growth. The company says it will use the capital to expand mass-production capacity and its team at its Dresden “Reloaded” facility, helping industrialize its GO-2 electric propulsion systems and meet rising demand from large satellite constellations. - learn more
- Machina Labs raised a $124M Series C to build its first large-scale “Intelligent Factory,” a U.S.-based production site aimed at rapidly manufacturing complex metal structures for defense, aerospace, and advanced mobility. The company says the funding, backed by investors including Woven Capital, Lockheed Martin Ventures, Balerion Space Ventures, and Strategic Development Fund, will help it scale its AI-and-robotics “software-defined” manufacturing approach from breakthrough tech into high-throughput production infrastructure. - learn more
- Midi Health raised a $100M Series D led by Goodwater Capital, with new investors Foresite Capital and Serena Ventures joining and existing backers including GV, Emerson Collective, and others returning, valuing the company at over $1B. The women’s telehealth provider says it will use the funding to scale beyond menopause care into a broader, AI-enabled women’s health platform, expanding access and using AI to personalize care and streamline clinical operations. - learn more
- Mitra EV raised $27M in financing, combining equity led by Ultra Capital with a credit facility from S2G Investments, to expand its “no upfront capital” fleet electrification model. The Los Angeles-based company says it will use the money to grow its shared charging network, roll out additional fleet solutions, and expand into new markets, positioning itself as a fully managed package that bundles EV leasing, overnight charging, and access to shared fast-charging hubs. - learn more
- Plug raised a $20M Series A to scale its EV-first marketplace, following $60M in used EV sales since launching in 2024. The round was led by Lightspeed with participation from Galvanize and existing investors including Autotech Ventures, Leap Forward Ventures, and Renn Global, as Plug positions itself as infrastructure for the coming wave of off-lease EV inventory with EV-native pricing, battery health insights, and faster dealer transactions. - learn more
- Breezy, a Los Angeles-based AI operating system for residential real estate professionals, raised an oversubscribed $10M pre-seed round led by Ribbit Capital, with participation from Fifth Wall, DST Global, Liquid 2 Ventures, O.G. Venture Partners, and others. The company says it will use the funding to strengthen its product and data platform, grow engineering and design, invest in security, and prepare for broader U.S. and international rollout. - learn more
LA Venture Funds
- Upfront Ventures participated in Daytona’s $24M Series A, a round led by FirstMark Capital with participation from Pace Capital and existing investors E2VC and Darkmode, plus strategic checks from Datadog and Figma Ventures. Daytona is building “composable computers” for AI agents, essentially programmatic, stateful sandboxes that can be spun up, paused, and snapshotted on demand so agents can safely run code and explore many paths in parallel at scale. - learn more
- Second Sight Ventures participated in Willie’s Remedy+’s $15M Series A, a round led by Left Lane Capital to fuel national retail expansion and continued product development for its hemp-derived THC beverages positioned as an alcohol alternative. The company says it has already sold 400,000+ bottles in under a year and claims the top spot for online THC beverage sales as it gears up for broader distribution in 2026. - learn more
- Navitas Capital led Cadastral’s $9.5M funding round, with participation from JLL Spark Global Ventures, AvalonBay, Equity Residential, and 1Sharpe. Cadastral says it will use the capital to accelerate product development and expand go-to-market for its vertical AI platform, positioning the product as an “AI analyst in a box” that automates core commercial real estate workflows like underwriting and due diligence. - learn more
- B Capital participated in Lunar Energy’s $232M raise, which the company disclosed as two rounds: a $102M Series D led by B Capital and Prelude Ventures, and a previously unannounced $130M Series C led by Activate Capital. The startup says it will use the capital to rapidly scale home-battery manufacturing and deployments, turning those distributed systems into a grid-supporting virtual power plant as electricity demand surges. - learn more
- B Capital participated in Goodfire’s $150M Series B at a $1.25B valuation, a round that also included investors like Juniper Ventures, DFJ Growth, Salesforce Ventures, Menlo Ventures, Lightspeed, South Park Commons, Wing, and Eric Schmidt. Goodfire says it will use the funding to scale its interpretability-driven “model design environment,” aimed at helping teams understand, debug, and deliberately shape how AI models behave in high-stakes settings. - learn more
- Helena participated in Positron AI’s oversubscribed $230M Series B at a post-money valuation above $1B, alongside strategic investors including Qatar Investment Authority and Arm. The round was co-led by ARENA Private Wealth, Jump Trading, and Unless, and the company says it will use the capital to scale energy-efficient AI inference now and accelerate its next-generation “Asimov” silicon roadmap. - learn more
- Smash Capital participated in ElevenLabs’ $500M Series D, which values the company at $11B as it scales its voice and conversational AI products for enterprise use. The round was led by Sequoia Capital with support from existing backers like Andreessen Horowitz and ICONIQ Capital, plus additional participation including Lightspeed Venture Partners. - learn more
- MTech Capital participated in Pasito’s $21M Series A, a round led by Insight Partners with additional participation from Y Combinator. Pasito says it’s building an AI-native workspace for group health, life, and retirement benefits that turns messy, unstructured plan and census data into a unified layer so carriers and brokers can automate workflows end-to-end, from quoting and enrollment to support and claims. - learn more
- Rebel Fund participated in Ruvo’s $4.6M seed round, led by 1confirmation with participation from Coinbase Ventures and others, as the Y Combinator-backed fintech expands its cross-border payments infrastructure between Brazil and the U.S. Ruvo says it operates like a U.S. dollar account for Brazilians, combining Pix, stablecoins, ACH/wire transfers, and a Visa card in one app to speed up remittances by reducing intermediaries. - learn more
- Rainfall Ventures participated in a seed funding round for Deft Robotics alongside Spring Camp, backing the company’s push to build AI-driven automation tools for manufacturers. The round amount wasn’t disclosed in the announcement, but the funding is positioned to help Deft scale product development and customer deployments in industrial settings. - learn more
- Trousdale Ventures participated in CesiumAstro’s Series C by leading the $270M equity portion of a $470M total growth-capital raise, alongside investors including Woven Capital, Janus Henderson Investors, and Airbus Ventures. CesiumAstro says the broader financing also includes $200M from Export-Import Bank of the United States and J.P. Morgan, and will fund a major U.S. scale-up including a new 270,000-square-foot HQ and expanded manufacturing to accelerate deployment of its software-defined, AI-enabled space communications platforms. - learn more
- Mucker Capital participated in Linq’s $20M Series A, which was led by TQ Ventures to help the company become infrastructure for AI assistants that run directly inside messaging apps. Linq’s platform lets developers and businesses deploy assistants through channels like iMessage, RCS, and SMS, and the company says the funding will go toward expanding the team, building a go-to-market motion, and continuing to develop the product. - learn more
- Sound Ventures participated in Day AI’s $20M Series A, which was led by Sequoia Capital with additional participation from Greenoaks, Conviction, and Permanent Capital. Day AI says the funding will help scale its AI-native CRM platform and support its move into general availability, positioning “CRMx” as a faster, context-driven alternative to legacy systems that turn simple questions into slow projects. - learn more
- Chaac Ventures participated in Arbor’s $6.3M seed round, which was led by 645 Ventures with additional backing from Next Play Ventures, Comma Capital, and angel investors. Arbor is building an AI interview and research platform that captures frontline employee and customer conversations and turns that qualitative “ground truth” into structured operational intelligence leaders can act on quickly, without slow surveys or pricey consultants. - learn more
- B Capital participated in When’s $10.2M Series A, a round co-led by ManchesterStory and 7wire, with new investor Mairs & Power Venture Capital and returning backers Enfield Capital Partners, TTV Capital, and Alumni Ventures. When says it helps employers and departing or transitioning employees navigate health coverage changes by steering people to more affordable alternatives to COBRA through an AI-powered marketplace and targeted reimbursements, with the new capital going toward team growth and expanding into more transition scenarios like Medicare eligibility and early retirements. - learn more
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