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.

https://twitter.com/spencerrascoff
https://www.linkedin.com/in/spencerrascoff/
admin@dot.la
Rain's Latest Funding Fuels the Future of Financial Wellness

🔦 Spotlight

Happy Friday,

This week, the LA tech scene buzzed with news that Rain, a leader in financial wellness, hassecured $75 million in Series B equity funding, spearheaded by Prosus. This isn't just another funding round; it's a pivotal chapter in Rain's mission to transform how American workers interact with their earnings.

Since its inception, Rain has been at the forefront of innovation in financial technology, particularly with its earned wage access solutions. The concept was simple yet revolutionary: allow workers to access their earned wages instantly, mitigating financial stress and dependency on high-interest payday loans. This vision quickly gained traction, propelling Rain from a promising startup to a key player in the fintech space.

What makes this Series B funding particularly noteworthy is what it represents on a larger scale. It's not just an influx of capital but a strong endorsement of Rain's potential to expand even further. With previous rounds fueling their initial growth and strategic partnerships, such as their notablecollaboration with Marqeta to enhance payment technologies, Rain has steadily built a foundation not just for success but for significant impact.

As Rain secures this significant new funding, their initiative to reshape financial wellness is set to expand dramatically, showcasing the profound impact tech can have on everyday financial challenges.

Looking forward to seeing how their innovations will drive change in the financial landscape.

🤝 Venture Deals

LA Companies

  • Dosen, a Los Angeles-based HRtech startup founded by Ronan Wall, Victor Burke, and Cian McCarthy, has secured $2.3M in an oversubscribed pre-seed funding round led by Affinity Ventures. The company offers an AI-powered platform that aligns employee-led learning with business goals through personalized, gamified development programs. The funds will be used to scale the platform, enhance AI-driven personalized learning, and improve employee engagement and productivity. - learn more
  • Plug, a Santa Monica-based company operating an EV-exclusive wholesale online auction platform, has secured $6.7M in an oversubscribed seed funding round led by Floodgate, Autotech Ventures, and A*. The company has also launched Plug Trade Desk™, the first EV-focused service designed to help dealers confidently price, move, and monetize trade-ins. The newly acquired funds will be used to enhance Plug's technology and expand its services, aiming to support dealers in navigating the growing used EV market. - learn more
  • Gallatin AI, a defense tech startup, has raised $15M in seed funding led by 8VC to scale its AI-powered logistics platform, Navigator. The tool helps military logisticians predict, plan, and execute operations more efficiently in contested environments. Funds will be used to expand the team and deploy the platform across military services. - learn more
  • BLNG AI, a generative AI platform based in Los Angeles and Paris, raised $3M in seed funding led by Speedinvest to streamline jewelry design by turning sketches into photorealistic renderings and animations. The funding will support commercialization, team expansion in Europe and the U.S., and the launch of a subscription-based app for luxury brands and independent jewelers. - learn more
  • Amca, a newly launched aerospace company focused on modernizing the industrial supply chain, has raised $76M in funding from investors including Caffeinated Capital, Founders Fund, Lux Capital, Andreessen Horowitz, and others. The company plans to acquire specialized suppliers and develop new aerospace products, aiming to strengthen and future-proof the sector’s manufacturing and innovation capabilities. - learn more
  • Turbine Finance Corp., a Santa Monica, California-based data science-driven liquidity platform, has raised a total of $21.75M in equity funding, comprising a $13M Series A round co-led by Alpha Edison and TTV Capital, and a previously unannounced $8.75M seed round with participation from Fin Capital, B Capital, and Sozo Ventures. Additionally, the company secured up to a $100M warehouse facility from Silicon Valley Bank to provide credit facilities to venture investors. The combined funding of $121.75M will be used to deploy the warehouse line and expand Turbine's data science team. Turbine's platform enables private equity and venture firms to offer limited partners access to the value of their portfolio investments without reducing exposure, leveraging machine learning to expedite underwriting processes. - learn more
  • Gente Beauty, an innovative Brazilian body care brand, has received a lead investment from Webster Capital, a private equity firm specializing in consumer and healthcare sectors. This partnership aims to support Gente Beauty's growth and expansion in the beauty industry. - learn more
            LA Venture Funds
            • Alexandria Investment Partners participated in a $41M Series A round for Solu Therapeutics, a Boston-based biotech company developing targeted protein degradation therapies. The funding will advance its lead candidate, STX-0712, which recently entered a Phase 1 clinical trial for CMML and other advanced blood cancers. - learn more
            • Calibrate Ventures participated in SigIQ.ai's $9.5M seed funding round. SigIQ.ai, based in Berkeley, California, is an AI tutoring startup focused on providing personalized education through advanced AI models. The funds will be used to hire top talent, enhance their AI models, and scale their platforms to educational systems worldwide. - learn more
            • Rusheen Capital Management participated in Zero Industrial's $10M Series A funding round, aiming to accelerate the development of thermal energy storage solutions in North America. Zero Industrial focuses on deploying large-scale thermal energy storage projects to enhance energy efficiency and support decarbonization efforts. The funding will be used to expand their project pipeline and advance the commercialization of their technology. - learn more

            LA Exits

            • Bread Beauty Supply has been acquired by Cost of Doing Business (CODB), a holding company founded in 2024 by Topicals founder and CEO Olamide Olowe and president Sochi Mbadugha. The acquisition aims to expand Bread's retail presence in the U.S., starting with an increased footprint in Sephora stores. Founder Maeva Heim will continue as Chief Creative Officer, focusing on the brand's creative direction, while CODB will manage strategic operations. This move reflects CODB's commitment to supporting Black-owned businesses and fostering diversity in the beauty industry. - learn more

                          Download the dot.LA App

                          El Segundo Startup Turns Tax Credits into Big Business

                          🔦 Spotlight

                          Hello LA,

                          Step into the world of Incentify, the El Segundo-based innovator turning the headache of managing tax credits and incentives into a walk in the park. Founded in 2019, this trailblazing company is reshaping how businesses approach what was once a daunting bureaucratic challenge.

                          Incentify’s platform is revolutionizing the industry by helping businesses discover and effectively manage a share of the estimated $1.2 trillion in tax credits and incentives that often go unclaimed each year. This critical service not only simplifies the process but also ensures that companies can more easily access and leverage these financial opportunities to fuel their growth and sustainability initiatives.

                          Recently, Incentify reached a new milestone by securing $9.5 million Series A funding led by Innovent Capital Group. This significant investment underscores the market’s confidence in their innovative approach and supports their mission to expand their technological capabilities and market reach.

                          As Incentify gears up for this expansion, their efforts are set to make tax incentives more accessible to a broader spectrum of businesses. This is especially vital in today’s economy, where optimizing financial strategies is crucial for business resilience and growth.

                          Incentify's success story from El Segundo is not just about financial gains but also about empowering companies with the tools to turn complex financial engagements into strategic advantages.

                          Stay tuned for more from LA’s vibrant tech scene. Let’s continue to push the boundaries of what’s possible.

                          Enjoy your weekend, and keep innovating, LA!

                          🤝 Venture Deals

                          LA Companies

                          • TOGETHXR, a pioneering women's sports media and commerce brand co-founded by athletes Alex Morgan, Chloe Kim, Simone Manuel, and Sue Bird, has achieved profitability and significant growth, including tripling its year-over-year revenue and increasing its social media following by 17% year-to-date. The company has secured additional growth capital in a funding round led by Alex Morgan's Trybe Ventures. The funds will be used to expand TOGETHXR's presence in the women's sports marketplace. Additionally, media executive Nancy Dubuc has joined the company as Executive Chair, bringing her extensive experience to support TOGETHXR's mission of elevating women's sports and culture. - learn more
                          • Airvet, a Los Angeles-based pet telehealth platform, has secured $11M in an oversubscribed Series B-2 funding round led by HighlandX. This investment follows a year of significant growth, including a 4x increase in year-over-year revenue and a tripling of its client base. Airvet partners with leading employers across various industries, such as PepsiCo, Adobe, and Lyft, to provide employees with 24/7 access to veterinary care via video or chat. The platform's services include online pharmacy, e-prescriptions, discounted pet insurance, wellness programs, and specialty care, with recent expansions into Spanish and French language support. The funds will be used to further enhance Airvet's platform and expand its reach, aiming to make veterinary care more accessible and affordable for pet families globally. - learn more
                                  LA Venture Funds
                                  • Interlagos co-led a $50M Series A funding round for Aetherflux, a San Carlos, California-based startup developing satellites to collect and transmit solar energy from space to Earth. The funds will be used to expand Aetherflux's engineering team and advance the technology for its planned low Earth orbit demonstration mission in 2026. - learn more
                                  • Bungalow Capital Management co-led a $2M seed funding round for Juno, a Denver-based startup specializing in corporate guest travel management. Juno offers an integrated platform that streamlines booking, logistics, payments, reimbursements, and support for non-employee travelers such as job candidates, contractors, and customers. The funds will be used to accelerate product development and expand partnerships, including a collaboration with ALTOUR as their first travel management company partner. - learn more
                                  • Veridical Ventures co-led a $3.75M seed funding round for Flagship, a Sydney, Australia-based retail technology company specializing in visual merchandising solutions. Flagship's platform creates digital twins of retail stores, enabling data-driven optimization of product placement and store layouts to enhance sales performance. The funds will be used to expand Flagship's presence in the U.S. market and further develop its product offerings. - learn more
                                  • Miroma Ventures participated in a £6.5M Series A funding round for Limitless Travel, a Birmingham, UK-based company specializing in accessible holidays for individuals with disabilities. Founded in 2015 by Angus Drummond, who was diagnosed with muscular dystrophy at 22, Limitless Travel offers curated group holidays with trained carers, ensuring accommodations and excursions meet specific accessibility needs. The investment will enable the company to enhance its technology, expand its range of destinations, and lay the groundwork for international growth, aiming to transform the lives of disabled individuals through travel. - learn more
                                  • B Capital participated in a $20M Series A funding round for Gable, a Seattle-based company specializing in data management solutions. Gable's platform focuses on "shifting left" in data management by enabling software and data developers to collaboratively build and manage high-quality data assets through API-based data contracts. The funds will be used to accelerate product development and expand Gable's team to meet the growing demand for data collaboration tools. - learn more
                                  • Rebel Fund participated in a $3.8M funding round for Sohar Health, a health technology company. Sohar Health is developing an AI-powered platform designed to streamline patient intake and triage, aiming to enhance access to healthcare services. The funds will be used to accelerate product development and expand the company's reach within the healthcare industry. - learn more

                                      LA Exits

                                      • Tixologi, a next-generation ticketing platform, has been acquired by Punchup Live, a New York-based comedy platform. This strategic move integrates Tixologi's advanced ticketing technology into Punchup Live's ecosystem, enabling seamless, direct-to-fan ticket sales for comedians and venues. The acquisition aims to enhance the ticket purchasing experience by providing features such as fast checkout, unified outreach tools, and advanced anti-scalping solutions, thereby empowering comedians to connect more effectively with their audiences. - learn more
                                      • InVisit, a Calabasas, California-based provider of cloud-based visitor management solutions, has been acquired by Motorola Solutions. InVisit's platform streamlines visitor registration, access, and host notifications across sectors such as commercial offices, education, and healthcare, enhancing security through features like blocklist screening and real-time guest activity insights. This acquisition aims to integrate InVisit's capabilities into Motorola Solutions' Avigilon Alta security suite, offering enterprise customers a unified, cloud-native approach to managing security threats and improving operational efficiency. - learn more

                                                  Download the dot.LA App

                                                  $207M Later, Napster is Back and Ready for the Metaverse

                                                  🔦 Spotlight

                                                  Happy Friday, Los Angeles!

                                                  This week, we’re rewinding the clock and fast-forwarding into the future at the same time. Napster, yes, that Napster, just got acquired for $207 million byInfinite Reality, a metaverse and immersive tech company that’s aiming to bring the iconic music platform into the next generation.

                                                  For anyone who came of age in the early 2000s, Napster was either your musical awakening or the reason your dial-up connection crashed. Launched in 1999 by Shawn Fanning and Sean Parker, it was the face of peer-to-peer file sharing and a lightning rod in the music industry’s first wave of digital disruption. After its legal battles and shutdown in 2001, Napster bounced between owners like Roxio and Best Buy, before eventually merging with Rhapsody and evolving into a legitimate streaming service.

                                                  Now, Infinite Reality is giving Napster a fresh remix. The company says it plans to turn Napster into a social-first music platform that emphasizes artist-fan interaction over passive listening. We’re talking virtual 3D concert experiences, listening parties, fan communities, and merch drops… essentially, a metaverse-native platform built for music superfans.

                                                  According to Infinite Reality CEO John Acunto, this aligns with the company’s bigger vision: moving the internet away from “a flat 2D clickable web” into “a 3D conversational one.” They’re betting that a brand like Napster, which already carries cultural weight, can thrive in a world where fans want deeper connections and creators want modern monetization tools.

                                                  It’s a bold move, but maybe a smart one. Nostalgia is a powerful asset, and in an era where legacy brands keep getting digital reboots, Napster has a chance to go from early disruptor to comeback story.

                                                  Will today’s listeners hit play? We’ll see. But as far as tech comebacks go, we’re here for this remix.

                                                  🤝 Venture Deals

                                                  LA Companies

                                                  • Topanga, a Los Angeles-based company specializing in AI-driven waste reduction solutions for commercial kitchens, has raised an $8M Series A funding round led by Blue Bear Capital, with participation from Struck Capital, Amasia, and Wonder Ventures. This investment brings Topanga's total funding to $12.2M. The company plans to use the proceeds to expand its food waste tracking platform into the senior living, health care, and hospitality sectors, accelerate the growth of its ReusePass system beyond universities into enterprise food service, and enhance integration with major food-service platforms like Grubhub and Jamix. - learn more
                                                  • Flight Science, an aviation tech startup focused on AI-powered flight optimization, raised $1.5M in pre-seed funding led by Outsiders Fund. The company helps airlines reduce fuel costs, emissions, and turbulence impact, and will use the funds to grow its team and expand product rollout by summer 2025. - learn more
                                                        LA Venture Funds
                                                          • Second Sight Ventures participated in a $14.2M Series A1 funding round for Lucky Energy, an Austin, Texas-based energy drink company. Lucky Energy offers a line of zero-sugar, zero-calorie beverages in six flavors, formulated with ingredients like maca and beta-alanine. The company plans to use the funds to accelerate distribution, introduce new products, support strategic partnerships, and recruit in key business areas. - learn more
                                                          • M13 led a $5.5M funding round for Chord Commerce, with participation from Act One Ventures and others. The New York-based company provides an AI-powered customer data platform (CDP) that helps commerce brands unify customer data, generate real-time insights, and automate marketing decisions. The funding will be used to further develop the platform and support brands in scaling their data-driven marketing efforts. - learn more
                                                          • Upfront Ventures led a $4M Seed funding round for Arlo Health, a New York City-based AI-powered health insurance underwriter focused on small and mid-sized businesses. Arlo offers level-funded health plans designed to improve preventive care and cost transparency through value-based care and AI-driven underwriting. The funds will be used to expand its broker network, grow its engineering and sales teams, and scale operations. - learn more
                                                          • Bonfire Ventures co-led a $5M Seed funding round for VoiceOps, with participation from Village Global and others. Based in New York City, VoiceOps uses generative AI to analyze phone calls and surface insights that boost sales performance, ensure compliance, and optimize marketing. The funding will support product development, team expansion, and broader market adoption. - learn more
                                                          • MANTIS Venture Capital participated in a $17.2M Seed funding round for EDGE Markets, a fintech company building banking tools tailored to the gaming industry. EDGE’s flagship product, EDGE Boost, offers a debit card and bank account specifically designed for betting, with features like spending limits, financial transparency, and cash-back rewards. The funds will be used to further develop the platform and expand its presence within the gaming market. - learn more

                                                              LA Exits

                                                              • SmartDepo, a leading provider of AI-powered deposition summaries for the legal industry, has been acquired by Rev, a prominent speech-to-text technology company. Founded in 2023 by civil rights attorney Isaac Manoff, SmartDepo delivers comprehensive deposition summaries featuring 100% accurate page-line citations, hyperlinked tables of contents, key admissions analyses, and deposition memos highlighting essential themes. This strategic acquisition combines Rev's highly accurate transcription services with SmartDepo's advanced summarization capabilities, aiming to enhance productivity for attorneys and court reporters by reducing manual review time and improving client outcomes. - learn more
                                                              • Stem, a platform offering personalized distribution and digital strategy services for independent artists and labels, has been acquired by Concord, a leading independent music company. Stem will operate as a separate division within Concord Label Group, with CEO Milana Lewis and President Kristin Graziani continuing in their roles. This acquisition provides Stem with the capital and resources to invest in new technology, expand its suite of label services, and accelerate global growth, while maintaining its mission to empower independent artists with autonomy and support. - learn more

                                                                          Download the dot.LA App

                                                                          RELATEDEDITOR'S PICKS
                                                                          Trending