How To Startup Part 8: Exits

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.

How To Startup Part 8: Exits
Image by Master1305/ Shutterstock

Welcome to the last installment in the “How To Startup” series and an often overlooked step when creating a business: exiting. In short, an exit strategy is exactly what it sounds like - a way out, sort of. I say sort of because frequently a sale of a company is just a new beginning, but more on that below. Startups usually seek an exit to generate investment returns for their investors and shareholders (usually including their employees), or sometimes to limit losses. It is important for founders to keep the possibility of an exit in the back of their minds at different stages of the business’ growth. Some startups are “big swings” where founders and their investors believe the idea and the team have the potential to turn the company into a multi-billion dollar public company. But many startups are smaller ideas where a smaller sale is a good outcome and is something always to be explored. It is important for founders to know which of these best describes their company.


As we’ve already learned in previous installments, the most successful entrepreneurs are the ones who plan ahead. So now that your company has traction and growth—or you’re a proactive entrepreneur who wants to get ahead—it’s time to think about an exit for the business.

Types of Exits

There are many different common exit strategies, but ultimately the one you choose will depend on your own business, personal and financial goals. I cover some of the pros and cons of each strategy below.

Liquidation

Failing, but “failing fast” and liquidating can sometimes be the best route to minimize losses for a business. You’ll likely find yourself in one of two scenarios when considering a liquidation: you’re already at the end of your rope - be it financially or otherwise - or you can see the end coming. If you’re fresh out of cash, evaluate how you can responsibly wind down the business for all parties involved - yourself, employees and investors. If you can tell early on that you don’t have product-market fit or traction and you still have cash left, plan to exit early and return money to investors. A great example of this is when Jeffrey Katzenberg returned $350M to investors instead of simply running Quibi until it was out of cash.

Sale or Acquisition

If you plan to sell your company (a.k.a. if it is getting acquired), you can receive payment from the acquirer in cash, stock or a combination of both. The acquirer can pay you cash for the company or you can exchange your stock in your company for shares of stock in the newly combined company. This will let you maintain being an active participant and shareholder as the company continues to grow. It’s not common in tech for acquisitions to involve both cash and stock. If you believe the company is poised to continue scaling, then definitely consider receiving stock as a part of the transaction. A famous example of this is when Facebook purchased Whatsapp for $4B in cash and $12B in Facebook shares in 2014, helping them grow into developing markets. The Facebook stock that Whatsapp shareholders received ended up being worth many multiples of the $12B which it was valued at during the time of the deal.

The amount a startup can sell for is determined by a few factors. Here are a couple of examples of how valuations are determined:

- If it’s a small company worth <$10M, it’s probably an acquihire (the process of acquiring a company primarily to recruit its employees). In this case, acquirers usually value the target based on how many engineers or product people are at the company.

- If it’s a deal worth <$100M, it’s usually priced more on strategic fit than real analysis such as what the target brings to the acquirer. This could be technology, a great team, a new business line they can build on, great potential of the merger, etc. For example, when I was CEO of Zillow we acquired 16 companies, most of which were in the $10M-$100M price range, and we always determined fair value by focusing on the overall level of strategic fit of the target more than evaluating the actual financial results of the target.

- If it’s a bigger deal with >$100M, the target’s financial results are usually benchmarked against other public comps and require real math to analyze. At deals of this size, advisors such as investment bankers usually participate in the deal and bring the analytical rigor and external perspective needed to evaluate the fairness of the deal for both sides.

Sometimes a sale is the end of the road for a company. But more often than not, it is just the beginning of the next chapter. For example, when Zillow acquired StreetEasy, the leading real estate portal in New York, we invested significant resources to grow the company after the acquisition. We added headcount, rebranded the company, invested in advertising and grew it substantially post-acquisition. Far from the sale being the end of the company, it was really just the beginning. Another example is Google’s acquisition of YouTube in 2006 for $1.65B of stock. At the time, YouTube was struggling with a myriad of legal and copyright infringement issues from content owners and was struggling to keep up with user demand. Under Google’s ownership, YouTube cleaned up its content copyright issues, invested tens of millions of dollars in technology to improve the service, and today YouTube is probably worth at least $100 billion under Google’s ownership and stewardship.

Initial Public Offerings (IPOs)

Traditional: Taking a company public is one of the ultimate goals for many founders, but it’s not exactly the finish line. In fact, it’s quite the opposite. For example, I named our IPO preparation at Zillow “Project Step” to emphasize to the team that it was just a “step” along the way towards building a great business.

In an Initial Public Offering, a company sells shares for the first time to public shareholders, and the stock is then traded on a stock exchange. This can be beneficial for a few reasons, such as being able to raise capital, get research reports written about the company and create liquidity for your investors so they can sell their stock. On the flip side, IPOs can be expensive (the fees are usually 5-7% of the amount raised) and come with a lot of uncertainty. One of the biggest challenges with this method is that the IPO window can be open or closed, and is dependent on things out of your control.

If you do pick this method, a piece of advice I often tell founders is to act and operate like a public company well before you actually are one. More on this and IPOs at a later date as I’ll probably do a separate piece on it.

SPAC Merger: A Special Purpose Acquisition Company (SPAC) is another way for a company to go public. With a SPAC, a publicly traded company is created for the purpose of acquiring or merging with an existing private company. One benefit of going the SPAC route is that, for now, company projections are permitted to be shared with investors during a SPAC merger which allows investors insight into a company’s growth prospects. I say “for now” because the SEC is evaluating this and there is speculation that it will no longer be permissible in the future. Another advantage is that you can select your shareholders through the Private Investment in Public Equity (PIPE) process plus receive advice and “sponsorship” from the SPAC itself which can be helpful to the company. The cons of a SPAC process are that it can be difficult to get enough investor focus on the company once you’ve gone public in this way, and SPACs are currently out of favor with investors.

Direct Listing: In a direct listing, a private company converts into being publicly traded but doesn’t actually sell any shares. Companies that choose to go public using this method usually have different goals than those that use an IPO - specifically, they do not need to raise capital through the offering. Direct listings create liquidity for existing shareholders and are usually less expensive than an IPO, but companies miss out on the chance to raise money.

Lessons On Exits

No matter what route you end up taking, when preparing for an exit: Always aim to be on the radar and top of mind for acquirers, understand your cap table and the goals of your shareholders, utilize investment banks and investors as resources and hire great M&A lawyers.

Missed a part or looking to reread? Part 1: Ideation, Part 2: Naming Your Business, Part 3: How To Pitch, Part 4: Surviving A Downturn, Part 5: Minimum Viable Product, Part 6: Product-Market Fit, Part 7: Scaling or read them all.

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Hello Sunshine Sold for More Than $900M. Now Reese Witherspoon Is Buying It Back.
Image Source: Hello Sunshine

🔦 Spotlight

Hey there, LA.

In Hollywood, every successful story eventually gets a sequel. This one brings Reese Witherspoon back to the company she built.

Five years after selling control of Hello Sunshine in a deal worth more than $900M, Witherspoon is partnering with French production group Mediawan to buy back the Los Angeles media company.

The reported purchase price is in the low-to-mid eight figures, significantly below Hello Sunshine’s valuation when Candle Media acquired a controlling stake in 2021.

That difference tells a larger story than any single Hollywood transaction.

Hello Sunshine was one of the most prominent acquisitions made during the streaming boom, when platforms were spending aggressively and investors placed enormous value on production companies with recognizable founders, established audiences and libraries of intellectual property.

Witherspoon had built all three.

Founded in 2016, Hello Sunshine developed its business around stories centered on women, producing projects including “Big Little Lies,” “The Morning Show,” “Little Fires Everywhere” and “Daisy Jones & The Six.” It also turned Reese’s Book Club into an influential audience and discovery platform that now reaches 6.2 million readers and drives approximately $900M in annual U.S. book sales, according to the company.

By 2021, that combination of talent, intellectual property and direct audience access looked like the foundation of a next-generation media empire.

Candle Media, backed by capital from Blackstone, acquired Hello Sunshine as part of a broader effort to assemble a portfolio of entertainment brands. The company also purchased businesses including Moonbug Entertainment, ATTN: and Faraway Road Productions.

Then the streaming market changed.

Entertainment companies became more disciplined about content spending. The race to accumulate subscribers gave way to pressure for profitability. Production budgets tightened, consolidation slowed and some of the valuations assigned during the streaming boom became difficult to maintain.

Hello Sunshine’s return to founder-led ownership reflects how dramatically the media landscape has changed since 2021. It also gives Witherspoon an opportunity to regain greater influence over the company at a moment when its core assets may matter more than its former valuation suggests.

Under the new ownership structure, Hello Sunshine plans to refocus on premium film and television, Reese’s Book Club and new storytelling and distribution formats. Mediawan brings an international production network, while Witherspoon brings something harder to manufacture: a trusted personal brand and an audience willing to follow her recommendations from books to screens.

That relationship with consumers is increasingly valuable in a fragmented media market. Studios can finance productions. Streaming services can distribute them. Far fewer companies can reliably convince millions of people to care before a project is even released.

For Los Angeles, the deal reflects the increasingly fluid boundary between entertainment company, consumer brand and technology-enabled audience platform. The most resilient media businesses may not be those producing the greatest volume of content, but those that own a direct relationship with a specific community.

The first Hello Sunshine deal captured the optimism of the streaming era.

The second may offer a more focused model for what comes next, with the company once again guided by the founder who understood its audience from the beginning.

Hollywood loves a comeback story.

This time, the company is making one too.

LA Tech Week’s Final Stretch

Still making the most of LA Tech Week? We have organized the remaining events by location to make planning the weekend a little easier:

Event schedules may change, so confirm the latest details with the organizer before heading out.

More from this week’s LA startup and venture scene below.

🤝 Venture Deals

    LA Companies

    • Goodweek raised a $12M seed round led by Adara Ventures to expand its AI management platform for small and midsize businesses. The company brings tools such as ChatGPT, Claude, Gemini and Mistral into one governed workspace and will use the capital to accelerate sales and expand into Latin America and Asia. - learn more

    LA Venture Funds
    • Fika Ventures co-led Otter Health’s $8M seed round alongside Evidenced Capital, with participation from Slow Ventures, Metrodora, CoFound Partners, Patient Capital, SemperVirens and Layout Ventures. The startup will use the funding to scale its AI-powered platform, which helps healthcare payers and providers reduce unnecessary care and manage quality without relying as heavily on traditional prior authorization. - learn more
    • Nant Capital co-led Prolific Machines’ $50M Series B2 alongside Atoms & Bits, bringing the biotechnology company’s total funding to more than $100M. Prolific will use the capital to scale its light-controlled biomanufacturing platform, expand pharmaceutical and biotech programs and begin early work on tissue and organ fabrication. - learn more
    • Family Fund participated in Allara’s $30M funding round alongside new investors Camino Partners and Foreground Capital, while existing backers including Index Ventures and GV increased their commitments. The women’s healthcare company will use the capital to expand AI-enabled care, grow its provider and enterprise partnerships and advance research into hormonal, metabolic and reproductive conditions. - learn more
    • Vida Ventures participated in Soufflé Therapeutics’ oversubscribed $135M Series B, which was led by Juvia Group. The biotech will use the funding to move three lead programs into clinical trials for muscular dystrophy, heart failure and muscle and metabolic disorders while advancing its broader pipeline of targeted RNA therapies. - learn more
    • FJOR participated in LightSprint’s $6.1M seed round, which was led by 645 Ventures. The AI software platform will use the funding to expand its enterprise product and grow its engineering and go-to-market teams as it helps employees across departments make changes to company codebases while keeping engineers in control. - learn more
    • Muse Capital participated in Collective X Health’s oversubscribed $3.2M pre-seed round, which was co-led by Council Capital and Anthemis Female Innovators Lab Fund. The women’s health intelligence startup will use the funding to expand its female-focused research and data platform, meet growing enterprise demand and support new research aimed at closing the women’s health data gap. - learn more
    • Act One Ventures participated in Intake AI’s $2.5M pre-seed round, which was led by Kapor Capital. The startup is building AI agents that automate clinical-trial setup and operations, helping research teams turn protocols into documents, search study materials and transfer approved forms into existing systems. - learn more
    • M13 participated in Ultra’s $62M financing, which included a $50M Series A led by Framework Ventures. The Brooklyn-based robotics startup will use the capital to expand deployment of its AI-powered warehouse robots, which handle packing, sorting and other fulfillment tasks and have already processed more than 500,000 orders. - learn more

    LA Exits

    • Farcaster is being acquired by Balaji Srinivasan’s Network School from Neynar, marking the decentralized social network’s second change in ownership this year. The deal includes Farcaster’s app, protocol repositories and related products, with its new owner planning to introduce a rules-based “social smart contract” governing full participation on the platform; financial terms were not disclosed. - learn more
    • Creator Authority has been acquired by Billion Dollar Boy Group, bringing the agency’s B2B influencer marketing expertise and LinkedIn specialization into BDB’s global creator business. The deal will help Creator Authority scale its work with enterprise brands while strengthening BDB’s presence on the U.S. West Coast and expanding its B2B creator marketing capabilities; financial terms were not disclosed. - learn more
    • Burbank-based CareerArc was acquired by AI hiring platform Humanly, with financial terms undisclosed. The deal combines CareerArc’s recruitment marketing and social recruiting tools with Humanly’s AI-powered candidate engagement, screening and interviewing platform, creating a more connected system for employers managing high-volume hiring. - learn more
    • Ethiqly was acquired by Carnegie Learning from Owl Ventures and the company’s management, with financial terms undisclosed. Carnegie Learning plans to integrate Ethiqly’s AI-powered writing platform into its literacy offerings, helping students improve their writing while giving teachers greater visibility into the drafting, revision and learning process. - learn more

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      How to Navigate LA Tech Week 2026

      🔦 Spotlight

      Happy Friday, Los Angeles.

      Next week, hundreds of tech events will take over the city, bringing founders, investors, engineers and creators together from October 12 through 18.

      Calling LA Tech Week a conference does not quite capture the experience.

      Presented by Andreessen Horowitz, Tech Week is a decentralized collection of panels, workshops, demonstrations and gatherings hosted independently by startups, venture firms and technology companies. There is no convention center or central stage. The programming stretches from Santa Monica and Venice to Culver City, Downtown, El Segundo and beyond.

      In other words, the city is the venue.

      AI remains the dominant theme for 2026, appearing across enterprise software, healthcare, finance, media and the creator economy. The schedule also reflects industries where Los Angeles has built a particular advantage, including aerospace, defense, robotics, advanced manufacturing, entertainment and consumer technology.

      That range is what makes LA Tech Week distinct. It brings together the software companies shaping what comes next with the industries that already define Southern California.

      The challenge is deciding where to show up.

      Our advice: apply early and organize your schedule by neighborhood. Crossing from Santa Monica to Downtown may look manageable on a calendar created by someone who has never driven in Los Angeles.

      To help you spend more time meeting people and less time crossing the city, we have organized each day’s events by location:

      You can also browse the complete official LA Tech Week calendar.

      Plan carefully, but do not fill every minute. The best conversation of the week may be the one that was never on your calendar.

      More from this week’s LA startup and venture scene below.

      🤝 Venture Deals

        LA Companies

        • El Segundo-based Gallatin AI raised a $50M Series A from new and existing investors including 8VC and Silent Ventures, bringing its total funding to $70M. The defense technology startup will expand its engineering team and advance Navigator, an AI platform that helps U.S. military units coordinate vehicle readiness, supplies, medical logistics and other mission-support operations. - learn more
        • Pasadena-based quantum computing startup Oratomic raised a $475M Series B at a $5.4B valuation, just three months after its Series A. ARCH Venture Partners, Spark Capital, Khosla Ventures, Index Ventures, General Catalyst and Bezos Expeditions co-led the round, bringing Oratomic’s total funding to $775M as it works toward a commercially viable, fault-tolerant quantum computer by 2030. - learn more
        • Torrance-based Fortastra raised a $30M Series A led by First In, with participation from Upfront Ventures, Space Capital, Rsquared, Side Door Ventures, ATX Ventures and existing investors. The company will use the capital to develop its next-generation maneuverable spacecraft, expand its engineering and operations teams and scale production of systems designed to protect critical assets in orbit. - learn more
        • Parallel Systems raised a $100M Series C led by AVP, with participation from Hillspire, Agility Global, Cobalt Capital, Anthos Capital, Congruent Ventures, Riot Ventures and Collaborative Fund. Founded by former SpaceX engineers, the company will use the funding to scale production and commercial deployment of its autonomous, battery-electric Panther rail vehicles, which are designed to make short-haul freight more competitive with trucking. - learn more
        • Gaming studio Gardens Interactive secured more than $35M in a Series B led by Lightspeed, with participation from Sequoia Capital, Index Ventures, Accel, Innovation Endeavors, Zenith Capital and other investors. The company will use the funding to launch and operate its debut social role-playing “strandbox” game, an evolving multiplayer world shaped by players’ actions and interactions. - learn more
        • Outer Spaces raised an $8M pre-seed round led by Upfront Ventures, with participation from Unlock Venture Partners, Mucker Capital and Genius Ventures. The startup is developing outdoor furnishings with integrated solar panels and batteries, turning backyards into sources of clean energy and backup power. - learn more
        • Furientis raised a $25M seed round led by Benchmark at a reported $125M valuation, following a $5M pre-seed announced in May. The defense startup will use the capital to scale production of lower-cost missile interceptors designed to be assembled quickly with readily available components, with a long-term goal of producing 1,000 systems annually at each factory. - learn more
        • Hiyo raised a $20.8M Series B led by Constellation Brands, with returning investor Live Nation also participating. The nonalcoholic beverage company will use the funding to expand its adaptogen- and nootropic-infused social tonics across more than 13,000 retail locations while growing its presence at hospitality venues and live events. - learn more
        LA Venture Funds
        • Navitas Capital participated in Vesta’s $30M Series B, which was led by Conversion Capital and included backing from several major mortgage lenders and financial institutions. The company will use the funding to scale its AI agents across mortgage origination, automating tasks such as application reviews, underwriting decisions and closing-document checks. - learn more
        • MTech Capital led Nettle’s oversubscribed $4.8M seed round, with participation from Project A Ventures, Sure Valley Ventures, Portfolio Ventures and Ventures Together. The insurtech startup will use the funding to expand across the U.S. and Europe while growing its AI platform, which helps commercial insurers identify property risks, accelerate inspections and generate reports. - learn more
        • Bonfire Ventures doubled down on Santé by participating in the company’s $15M Series A, which was led by FINTOP and included other returning investors. The New York startup will use the funding to expand its AI-powered operating system for independent wine and liquor stores, which combines point-of-sale, e-commerce, payments, inventory and marketing tools in one platform. - learn more

        LA Exits

        • Winnow Solutions was acquired by Marina del Rey-based Spring Labs, with financial terms undisclosed. Winnow’s attorney-built library of more than 100,000 state and federal regulatory requirements will become a core part of SpringGRC, helping financial institutions connect changing laws directly to their compliance policies, controls and workflows. - learn more

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          LA Tech Week 2026: Sunday’s Event Lineup

          🔦 Spotlight

          LA Tech Week 2026 closes Sunday with one final day of events across Los Angeles. We have organized the remaining lineup by neighborhood so you can finish the week with a few last conversations before everyone returns to their regularly scheduled inboxes.

          ARTS DISTRICT

          12:00 PM

          CARSON

          12:00 PM

          CULVER CITY

          9:00 AM

          • Women in Cleantech & Sustainability Hike and Network: See Details Here
            Women in Cleantech & Sustainability

          6:00 PM

          • Founders pitch competition: See Details Here
            Biomorphix solutions, Nightingale regenerative

          HOLLYWOOD

          10:00 AM

          4:00 PM

          • AI International: Film, Music Video & Micro-Drama: See Details Here
            AI International Film Festivals

          MID CITY

          1:00 PM

          OTHER

          12:00 PM

          • ORGANIC LIFE LABS™ PRESENTS THE ALIGNMENT LAB: The Science of human performance: See Details Here
            The Blue Room Collective

          SANTA MONICA

          8:00 AM

          1:00 PM

          6:00 PM

          SOUTH LA

          2:00 PM

          • Future Builders : Family STEM Day: See Details Here
            Black L.A. Tech Week (Community Collective)

          VENICE

          10:00 AM

          12:00 PM

          • How to Raise Funds to Fund Any Business Using Digital Products.: See Details Here
            DN Events

          VIRTUAL

          5:00 PM

          WEST HOLLYWOOD

          3:00 PM

          Each session provides unique opportunities to gain insights, network, and explore various fields of tech innovation. For updates or more event information, visit the official Tech Week calendar.

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