Office Hours: 4 Ways To Be an Intentional Mentor

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.

Office Hours: 4 Ways To Be an Intentional Mentor

Mentoring done right is an enriching part of your career. As a two-sided relationship, you have both an opportunity to seek out mentors who provide knowledge and counsel and to be one yourself, and each of these exchanges has its benefits. Neither, however, should be forced to fit within the classic construct of mentorship, that of a seasoned veteran taking a green employee under her wings. In fact, sometimes mentorship is the opposite.

I owe much of my early career success to what I learned from mentors, but I also owe some of my more recent strengths and knowledge to my mentees. Our evolving workplace and technological norms means mentoring can happen in all sorts of ways, and if you're intentional about mentorship you can be both a mentor and a mentee throughout your career — and, importantly, learn from both roles. Here are four principles that guide my approach to intentional mentorship:


1. Learning Is a Two-Way Street.

Mentorship isn't and shouldn't be one-sided. If it's a drain on your time and you're a busy person, odds are you'll run out of time for it quickly. I always try to find something I can learn from those I mentor. On the outside this may sound a bit selfish, but it actually works to both our benefit. We feel like we're trading value, which inspires confidence in your mentee and emboldens them to ask for real help and guidance when they need it without feeling like an imposition. As a mentee, you might think at first glance that you have less to bring to the table because you typically have less experience. But look closer; you usually have something you take for granted that is immensely valuable to others.

Some of my most memorable and impactful mentees include my Pacaso colleague Whitney Curry, who, as Zillow's first social media hire, taught me the magic of Twitter and Facebook and put me on my path to being a social CEO; years later, Whitney hired Kat Parra, who to this day continues to help me figure out Snapchat and TikTok to stay current in my social footprint. I've provided career counsel to both of these pros over the years, but they've taught me a lot, too.

Recently, another former colleague of mine from Zillow, Racquel Russell, joined Bird's Board of Directors. Racquel comes from a political background and over the years has taught me so much about how government really works; to this day, I still use her as a resource, asking her opinion on whether I should donate to a campaign or what she thinks the chances are for a piece of legislation passing. In return, I've been a resource for her on career development and joining boards. We both benefit from our relationship, and because of that we're emboldened to ask for what we need from one another.

2. Broadcast What You Know.

A couple of years ago I wrote about how to "hack" mentorship and build your own perfect mentor by following leaders and other professionals you admire. As I said, mentorship doesn't have to fit into that (increasingly uncommon) archetype of being taken under someone's wing. Over the years I've followed the lead of Jeff Weiner on people management, Sheryl Sandberg on building thought leadership, Warren Buffett on shareholder communication and Jeff Bezos on communicating priorities. I don't really know any of these people, but the internet and all of their self-published or publicly available content makes it so I don't have to.

Much of the reason I am constantly teaching publicly through my podcast and blog posts is that it enables me to mentor others in this anonymous way. I'm hopeful that the advice and perspectives I post help others navigate career hurdles, whether it's figuring out how best to manage your first team, how to grow your startup or how to take your company public. I share the things I know because others have shared them with me, and I want to continue to feed into that virtuous cycle. You, too, can do that easily. If you're a great writer, tell others your formula and some keys to your approach. As I said earlier, you probably take your strengths for granted; others won't.

3. Speak Up — With Candor and Kindness.

Dara Khosrowshahi, now the CEO of Uber, was one of my first managers in my career. As a summer analyst 25 years ago at the investment bank Allen & Company, I learned from Dara (then a young associate) how to value companies and build financial models. He taught me how to become an expert on Lotus 123 long before there was Excel or Google Sheets. But Dara also taught me another incredibly valuable piece of advice: Don't wear suspenders to the office. I'd mistakenly thought Hollywood accurately portrayed Wall Street; Dara kindly corrected me and saved me from repeating that faux pas.

Often the role of the mentor goes beyond subject matter expertise; it's about teaching mentees decorum — how to act and behave in certain situations. It may feel awkward for you as the mentor to teach when presented with awkward circumstances, but take it from suspender-wearing Spencer — they will appreciate your help more than you realize.

4. Invite Others Into the Room.

Though there are always reasons for closed-door conversations on sensitive topics, there are often exchanges that would prove valuable opportunities for your mentees (or mentors!) to listen and learn. I am eternally grateful to one of my first mentors — my dad's friend, Fred Rosen, the legendary founder and longtime CEO of Ticketmaster. In 1990, Fred invited me as a know-nothing 15 year old to his executive offsite at the Four Seasons Biltmore in Santa Barbara. He let me be a fly on the wall for two days of intense management meetings with the leadership team at Ticketmaster. Looking back on that experience now, I probably only understood a small fraction of what was discussed, but it was an extremely impactful moment in my life which set me on a path towards my business career. Some kids visit the baseball Hall of Fame in Cooperstown and decide they want to be a baseball player; I was invited to the leadership offsite of a big company and decided I wanted to become a businessperson.

In my early 20s, my mentor Andy Snyder at Goldman Sachs taught me how to behave among company clients and CEOs simply by including me in meetings where I was able to soak in knowledge by watching their interactions. Greg Lee and Bruce Evans at Goldman Sachs would generously invite me into their offices and use speaker phone when negotiating M&A deals so I could listen and learn. In my time as CEO of Zillow, I often pinged junior members of my team to hover around and listen to strategic discussions among our senior leaders — in part because I wouldn't have to explain it to them later but also because it helped them see how we debated and worked through scenarios that would decide the fate of the company.

Our acceleration into a virtual environment can either hinder or help these opportunities, and the difference comes down to whether those of us in the room are intentional about inviting others to join. Our virtual meeting rooms have no capacity, but they're also not easily dropped into (you don't have people passing by as you do in physical offices). If you're sharing knowledge or having strategic (but not confidential) conversations, consider taking advantage of our virtual environment to invite others in.

Though the methods of mentorship may be changing, mentorship itself remains as critical as it's ever been for career development and personal growth for junior team members and seasoned leaders alike. We're all pressed for time, and mentoring often drops on the list of priorities, but if you find ways to engage in it — intentionally, through small actions within your existing schedule — you'll gradually find that mentoring becomes second nature and a lasting habit.

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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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