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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LA Tech Week 2025: Sunday’s Event Lineup

Here's the Sunday, October 19th lineup for LA Tech Week 2025, organized by location so you can easily explore events that fit your goals and schedule. Dive in and see what’s happening near you!

ARTS DISTRICT

3:00 PM

BEL AIR

3:00 PM – 7:00 PM

BURBANK

6:30 PM – 9:30 PM

CULVER CITY

9:00 AM – 5:00 PM

4:30 PM – 7:30 PM

INGLEWOOD

10:00 AM – 2:00 PM

  • Spinovation: The Future Is Femme, The Future is Frequency: See Details Here
    Sonder Impact, Black Women Spin, Sip & Sonder

KOREATOWN

12:00 PM – 3:00 PM

MARINA DEL REY

12:00 PM

  • Sunday Tech Brunch
    Sawubona

MID CITY

9:00 AM – 11:00 AM

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

SANTA MONICA

9:00 AM

10:00 AM

3:45 PM

4:00 PM – 7:30 PM

  • OFF THE HOOK Santa Monica Seafood Festival: See Details Here
    Spin PR Group, City of Santa Monica, Tech St.

6:00 PM

7:00 PM

  • Pritam: A Musical Legend - Live in Concert: See Details Here
    American South Asian Network

7:00 PM

  • Building AI workflow editor in React with Workflow Builder SDK: See Details Here
    Workflow Builder

7:00 PM

8:00 PM

  • Unlock Apple's Corporate Advantage for your Startup!: See Details Here
    iStore by St. Moritz

TOPANGA CANYON

3:00 PM

  • Dreamore Hike and Picnic: LA Tech Week: *Invite Only*
    Dreamore

VENICE

10:00 AM – 12:00 PM

  • Coffee, Walk, and Schmooze: See Details Here
    JFE (Jews For Entrepreneurship) Network

VIRTUAL (LA)

10:00 AM

  • Level Up with LinkedIn: A Student’s Guide to Networking & Opportunities (Virtual Event): See Details Here
    FIMAC

10:00 AM

WEST ADAMS

1:00 PM – 3:00 PM

For updates or more event information, visit the official Tech Week calendar.

Enjoy LA Tech Week 2025!

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LA Tech Week 2025: Saturday’s Event Lineup

Here's the Saturday, October 18th lineup for LA Tech Week 2025, organized by location so you can easily explore events that fit your goals and schedule. Dive in and see what’s happening near you!

BEVERLY HILLS

2:00 PM

CENTURY CITY

7:00 PM – 10:00 PM

CULVER CITY

9:00 AM – 5:00 PM

10:00 AM – 11:30 AM

1:00 PM

DTLA

7:00 PM

  • {MiniMax x Nakid x SkyPortalx}: TECH/MOTION/MUSIC/ART: See Details Here
    MiniMax (Hailuo AI)

10:00 PM – 2:00 AM

EL SEGUNDO

10:00 AM

  • Venture on the Green: *Invite Only*
    BLCK VC

4:00 PM

INGLEWOOD

7:00 PM

  • Valar Atomics, Durin and Discipulus Ventures - Night With A Nuclear Reactor: See Details Here
    Valar Atomics, Durin, Discipulus Ventures

MARINA DEL REY

8:30 AM

12:00 PM – 3:00 PM

5:00 PM

  • LOST iN Sunset Sail: Navigating the Tides of the Creator Economy & Media: See Details Here
    LOST iN

PASADENA

9:00 AM

PLAYA VISTA

2:00 PM – 4:00 PM

SANTA MONICA

7:00 AM

9:00 AM

  • Pedal & Network: Tech Cyclists @ LA Tech Week 🚵: See Details Here
    Instafill.ai

9:30 AM

  • Getty Center Guided Tour & (Optional) Photography Scavenger Hunt: See Details Here
    NEW MOON Impact Productions

10:30 AM – 11:30 AM

11:00 AM – 2:15 PM

12:00 PM – 5:00 PM

1:00 PM – 5:00 PM

1:30 PM

  • Self-Defense in Court and the Streets: See Details Here
    Santa Monica Striking, Luri Inc.

2:00 PM

  • SMARTUP 500: THE FIRST AT TECH WEEK LA - Launching the world’s first Startup Ranking: See Details Here
    Smart Times

2:00 PM

  • NLPs (No Lame Panels) The Creator X Founder Rooftop Party: See Details Here
    Startup Village, Sanctuary

3:00 PM – 4:00 PM

4:00 PM – 6:30 PM

  • Just Do It?: Helping Founders Perform Like Olympians: See Details Here
    Elite Psychology Group

5:00 PM

6:00 PM

6:00 PM – 9:00 PM

6:00 PM

6:00 PM – 9:00 PM

  • The Future of Hospitality: Poetry, Provenance & Passports: See Details Here
    Villa Kitchen, Airble, We Speak Dance, Techstars San Francisco

7:00 PM

  • 🚀 Investor x Founder Open Mic Pitches: See Details Here
    Feathr, Los Angeles Fun Events

7:00 PM

  • Life is a Pitch - LA Edition: *Invite Only*
    DeepMyst

TOPANGA CANYON

5:00 PM – 8:30 PM

  • Walk&Jam: Use AI to make art while hiking Topanga Canyon: See Details Here
    Formhaus llc, Wonderland Immersive Design

TORRANCE

1:00 PM – 4:00 PM

  • Crunches & Conversations Presented by The Differentials and KIS Training Studios: See Details Here
    The Differentials, KIS Training Studios

VENICE

1:00 PM – 4:30 PM

  • Beyond the Language Barrier: Exploring AI's Next Frontier: See Details Here
    Medusa AI

VENICE BEACH

8:00 AM – 12:00 PM

  • SŨRFED Club @ Venice Beach: Founders, Creators, Investors share the waves: See Details Here
    SŨRFED Club, Go Vitamins

WEST ADAMS

9:30 AM – 10:45 AM

  • Funders Shaping Democracy, AI & Media: See Details Here
    New Media Ventures, New Rising Ventures

WEST HOLLYWOOD

4:00 PM

6:00 PM – 8:00 PM

9:30 PM

  • Vibe Check Comedy Show, Tech Week Edition! @ Hollywood Improv: See Details Here
    Vibe Check Comedy

For updates or more event information, visit the official Tech Week calendar.

Enjoy LA Tech Week 2025!

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LA Tech Week 2025: Friday’s Event Lineup

Here's the Friday, October 17th lineup for LA Tech Week 2025, organized by location so you can easily explore events that fit your goals and schedule. Dive in and see what’s happening near you!

ARTS DISTRICT

8:30 AM – 12:00 PM

  • Power Day: Ideas, Pitches, Connections: See Details Here
    Los Angeles Cleantech Incubator (LACI)

6:00 PM

  • WEB3 GAMING IS DEAD - Happy Hour: See Details Here
    Plassa Capital, Yee-Haw Monster Trucks

BEVERLY HILLS

10:00 AM – 11:00 AM

1:00 PM – 2:00 PM

2:00 PM – 3:00 PM

3:00 PM – 4:00 PM

4:00 PM

6:00 PM – 9:00 PM

  • So you went viral, Now what? (pt II): See Details Here
    Verci, Study Fetch, TechSpace

8:00 PM

  • Private Pool: GP x LP x FO: *Invite Only*
    Visionlist Commons , Bay Area Innovest

BRENTWOOD

8:00 AM

  • Founders & Investors Hike: See Details Here
    Salehpour Legal, Technology Founders of America

CARSON

11:45 AM

  • Lightspeed x SVB Porsche Experience: *Invite Only*
    Lightspeed Venture Partners, SVB

CULVER CITY

8:00 AM – 6:00 PM

11:00 AM

1:00 PM

  • Surf Parks & Wave Pools: From Doja Cat to Mark Zuckerberg: See Details Here
    Surflytics

8:00 PM – 12:00 AM

EL SEGUNDO

11:30 AM – 2:00 PM

5:00 PM – 8:00 PM

HOLLYWOOD

10:00 AM

  • AI, Revenue, and Reality: How Fortune 500s Work With Startups That Ship: See Details Here
    Sunrise AI, OpenTable

12:00 PM – 2:00 PM

  • Unplugged: LA Tech Week Recharge Experience with TAY × Checked Out: See Details Here
    TAY Fitness, Checked Out

9:00 PM

INGLEWOOD

8:00 AM

  • TCSI Presents: Caffeine & Connections: See Details Here
    The Cyber Security Intellects Nonprofit

LONG BEACH

7:00 AM

MALIBU

10:00 AM

  • Great Leaders Podcast & Profiles: See Details Here
    NEW MOON Impact Productions, Origin Studios

12:30 PM

MARINA DEL REY

9:00 AM

  • Keeping Your Freedom as a Founder: Real Talk on Funding: See Details Here
    Lighter Capital

10:00 AM – 1:00 PM

  • D-Wave Research Day & Hackathon!: See Details Here
    USC Information Sciences Institute, D-Wave

4:00 PM – 6:00 PM

  • The Sky is Not the Limit: All About Aerospace: See Details Here
    Sunstone Management, USC Viterbi Startup Garage

PASADENA

10:00 AM – 1:00 PM

11:30 AM – 1:30 PM

  • Deep Tech Entrepreneurship Pillars of Pasadena Tech: See Details Here
    Innovate Pasadena, Pasadena SBDC, City of Pasadena

PLAYA VISTA

9:00 AM

12:00 PM – 2:00 PM

  • Vision to Venture - AI Media Showcase powered by Google AI: See Details Here
    Google

SANTA MONICA

7:00 AM – 8:30 AM

  • Signal Run : RTC x Wildwood VC: See Details Here
    Run Tech Club, Wildwood Ventures

7:30 AM

8:45 AM – 10:45 AM

9:00 AM – 11:00 AM

  • Slash Burn Rates & Scale Your Startup: See Details Here
    Arizona Commerce Authority (ACA)

9:00 AM

  • Driving a Digital Ecology Relay: What is at Stake: See Details Here
    The PORT GLOBAL, GLOBAL PORTAL INSTITUTE

9:30 AM – 11:30 AM

10:00 AM – 1:00 PM

  • The Enduring Value of Inclusive Capital: See Details Here
    Founders Registry. Nervana

10:00 AM – 12:00 PM

10:30 AM

11:30 AM – 1:00 PM

  • Advisors to Investors Lunch: Venture Capital for enterprise leaders: See Details Here
    Collinear Capital, Worlds

12:00 PM

  • Powerhouse Capital & a16z speedrun Investor Lunch Mixer: See Details Here
    Powerhouse Capital, a16z, speedrun

2:00 PM

  • Where Robotics Meets Heart - Embedding Family Values in a Future with AI: See Details Here
    Trove, Puerto Rico Blockchain Association, MindfulBytes

2:00 PM

3:00 PM

3:00 PM

3:00 PM

  • Workshop: Create An Enterprise Chatbot and Unlock the 70% of Data Data You’re Not Using: See Details Here
    Aparavi

4:00 PM

5:00 PM – 10:00 PM

5:30 PM

5:30 PM – 9:30 PM

6:00 PM – 8:30 PM

  • USC Alumni Founders & Investors: See Details Here
    USC Alumni Entrepreneurship Network, Techstars

6:00 PM

  • Social Currency Series/Greenlit presents PitchPop: See Details Here
    Social Currency Series, Greenlit

6:00 PM – 9:00 PM

6:30 PM

6:30 PM – 10:00 PM

6:30 PM

  • Lets get the LA Bioeconomy brewing: See Details Here
    Founders, Friends & Fermentation, Saku Biosciences

7:00 PM – 11:30 PM

7:00 PM – 10:00 PM

7:00 PM – 10:00 PM

7:00 PM

7:00 PM

  • Liquid Equity 2: The Premiere Gathering for Founders, Creator
    Coeus Collective

7:00 PM

7:00 PM

  • For the Love of Tech | Speed Dating for Tech Professionals: See Details Here
    Feathr, Los Angeles Fun Events

7:00 PM

SOUTH LA

3:00 PM

TORRANCE

9:00 AM – 11:00 AM

  • The Future of Space & Security Panel: See Details Here
    Northwood Space, Anduril Industries, Impulse Space, Astranis

VENICE

9:00 AM – 10:45 AM

9:00 AM – 11:30 AM

11:00 AM

11:30 AM – 2:30 PM

12:30 PM

  • Creative Partners: Human + AI Storytelling: See Details Here
    Othelia, Primordial Soup

2:00 PM – 3:45 PM

5:00 PM

  • EarthHouse: Critical Minerals, Mobility & Modern Power: See Details Here
    The Strategye Group, Alpha Sierra One

6:00 PM – 9:00 PM

6:00 PM

  • Pizza+Soda: *Invite Only*
    Schmoozd , The KINN

7:00 PM

VENICE BEACH

2:00 PM – 6:30 PM

5:00 PM

8:30 PM – 2:00 AM

VIRTUAL (LA)

2:30 PM – 4:00 PM

3:00 PM

  • Government of Alberta: ProcurementAsCode // Done in 60 Seconds: See Details Here
    Government of Alberta

4:00 PM

  • Stop Hitting Yourself 🥊: See Details Here
    Stop Hitting Yourself, HOWDY, Company Policy, Snowbird Global

WEST HOLLYWOOD

3:00 PM – 6:00 PM

6:00 PM

WESTSIDE

5:00 PM

5:30 PM – 8:30 PM


For updates or more event information, visit the official Tech Week calendar.

Enjoy LA Tech Week 2025!

Download the dot.LA App


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