Office Hours: ComplYant Founder and CEO Shiloh Johnson On the Business of Taxes

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.

Shiloh Johnson in a suit
Shiloh Johnson

On this episode of Office Hours, ComplYant founder and CEO Shiloh Johnson talks about the challenges of running a fully remote business and the importance of supporting other minority founders.



ComplYant is a tax management platform that offers small business owners and entrepreneurs a simple way to better manage their taxes.

Johnson built ComplYant in 2019 — the first year of the pandemic. Building and running a company that’s fully remote comes with some challenges.

“Communicating with this large group of people to build this product every single day and all you're doing is communicating digitally, you're missing human elements,” she said. “When you're missing that, it is a sacrifice. There’s messages lost in text that wouldn't be lost face to face and there is just this constant battle because everyone at the company is super passionate about doing something really great, which is a great problem to have.”

With a Master’s degree in taxation and over 20 years of tax and corporate experience, Johnson has learned that many large corporations usually run their taxes in-house.

“So what I did is I worked in those spaces and I would take on all new lines of business,” she said. “I would take that new line of business and then I would go source all the tax abilities for that new line of business and then I would prepare the company to be tax compliant across all of its entities wherever locations they operate out of all over the world.”

Johnson created her own “cheat sheet” to remember the tax rules for each state.

“So like in Alabama, if you don't actually get your business license, they kick you out of town,” she explained. “They're very strict… I basically turned that cheat sheet into a product once I left corporate. I started my own practice, and I got all these small businesses that just had never heard of tax.”

But it wasn’t until she felt undervalued in her previous role as a tax supervisor that she considered branching out on her own.

“It proved something to me in that moment,” she said. “I'm good enough to do this on my own from start to finish. I could source the tax, I could pay the tax and then I could defend the tax. So I knew I could do the full cycle.”

Despite not having any tech or product background, Johnson had business expertise in taxes and was confident she had the knowledge to get ComplYant off the ground.

In the first year, she said she was “showing people what I was trying to do and then connecting the dots between what businesses would understand that to be.”

She added, “I immediately knew if I could just get one person to understand it and put money towards it, even if it was 50 cents, then I was cooking with gas. People, especially small businesses, don't have a lot of money. They value very deeply what they put their money towards and it better be valuable if they're going to put money down.”

As a Black woman founder, Johnson said that her journey to becoming an entrepreneur is unlike other minority founder's because investors were actually receptive to her idea and believed in ComplYant’s potential.

“I think for a lot of minority founders, the difficult thing is to get the meetings,” she said. “The other part of that is actually making sure you're prepared for the meetings. I think all the time and attention is spent on preparing founders for those meetings, and that there isn't enough time into making sure they actually get the meetings and then actually get valid passes or valid looks at what they're building.”

dot.LA Reporter Decerry Donato contributed to this post.

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Billion-Dollar Milestones and Snapchat’s New Features

🔦 Spotlight

Happy Friday Los Angeles!

This week’s spotlight showcases LA’s thriving tech scene, featuring Snapchat’s latest feature updates and two local startups Liquid Death and Altruist, making TechCrunch’s Unicorn List for 2024.

Image Source: Snap

Snapchat’s recent fall updates bring fresh features, including a new iPhone camera shortcut for instant snaps, Halloween-inspired AI-powered Lenses, and Bitmoji costumes inspired by Mean Girls and Yellowstone. Bitmoji stickers now reflect trending Gen-Z expressions like “slay” and heart symbols for added flair in chats. Plus, the “Footsteps” feature on Snap Map allows users to track their past adventures privately, adding a nostalgic touch.

Image Source: Liquid Death

ICYMI, two LA startups joined the Unicorn Club—achieving valuations over $1 billion. Liquid Death, based in Santa Monica, is a canned water company with edgy branding and a humorous sustainability focus. Known for viral marketing and brand partnerships, it redefines bottled water as a lifestyle brand and environmental statement. In March, Liquid Death closed $67 million in strategic financing, raising its total funding to over $267 million and valuing it at $1.4 billion.

Image Source: Altruist

Altruist, a Culver City-based fintech platform, offers financial advisors streamlined tools to better serve their clients. With a user-friendly investment and account management platform, Altruist has gained strong traction in the finance world. In May, it announced a $169 million Series E funding round, bringing its total funding to over $449 million and earning a valuation of $1.5 billion.

Together, Liquid Death and Altruist exemplify LA’s capacity for innovation across diverse sectors, from lifestyle branding to fintech. Whether reshaping financial tools or redefining sustainable branding, these companies showcase LA’s unique entrepreneurial spirit. Go LA!

Check out TechCrunch’s 2024 Unicorn List here. And don’t miss Snapchat’s latest features—perfect for adding some fun, connection and maybe a few selfies this weekend!


🤝 Venture Deals

LA Companies

  • Freeform, a company bringing AI to metal 3D printing, raised $14M in funding from NVIDIA’s NVentures and AE Ventures to further develop its AI-powered 3D printing technology for industrial-scale production. - learn more
LA Venture Funds
  • Anthos Capital participated in a $70M Series D round for Carbon Robotics, which develops AI-powered robotics for precision agriculture, and the funding will be used to accelerate the growth of its autonomous weeding technology. - learn more
  • Anthos Capital participated in a $3.5M seed round for Plasma Network, aimed at expanding access to USDT stablecoins on the Bitcoin network, with the investment supporting the network’s growth and efforts to enhance stablecoin accessibility through the Lightning Network. - learn more

LA Exits


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      ⚖️FTC’s "Click to Cancel" Rule and Its Ripple Effect on Tech

      🔦 Spotlight

      Happy Friday Los Angeles,

      The FTC’s new “Click to Cancel” rule is shaking up subscription-based tech. Now, instead of navigating a maze of cancellation hurdles, users can cancel subscriptions as easily as they signed up—with a single click. This shift is a wake-up call for SaaS, streaming, and app-based companies, where once-hidden exit options often kept users around simply because canceling was a hassle.

      The rule also requires businesses to send regular renewal reminders, ensuring customers stay informed about upcoming charges. It's more than a cancellation button—it’s about transparency and giving users control over their decisions.

      For startups, the impact goes deeper than UX adjustments. Many have relied on "dark patterns," which subtly discourage cancellations by hiding the exit. Now, companies must shift toward building genuine loyalty by delivering real value, not by complicating exits.

      While this might affect retention rates initially, it could lead to more sustainable business models that rely on satisfaction-driven loyalty. Investors may start prioritizing companies that emphasize transparent, long-term engagement over those that depend on dark patterns to maintain retention metrics.

      The rule opens the door to more ethical UX design and a truly user-centered approach across the tech industry. It may even set a precedent against manipulative design in other areas, such as privacy settings or payment methods.

      Ultimately, the “Click to Cancel” rule presents an opportunity for the tech industry to foster trust and build stronger customer relationships. Startups and established companies that embrace transparency will likely stand out as leaders in a new era of customer-centric tech, where trust—not tricky design—is what retains users.

      As the tech landscape continues to evolve, LA Tech Week 2024 offers a chance to explore these shifts in real-time. Check out the upcoming event lineups to stay informed and make the most of your time:

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


      🤝 Venture Deals

      LA Companies

      • Ghost, a company supporting top brands and retailers with streamlined logistics and fulfillment solutions, raised a $40M Series C funding round led by L Catterton to fuel its continued growth and innovation. - learn more

      LA Venture Funds
      • Assembly Ventures participated in a $27M Series A round for Monogoto, a provider of software-defined connectivity solutions that enable secure, cloud-based IoT and cellular network management on a global scale. - learn more
      • Angeleno Group participated in a $32M Series C round for REsurety, a company that recently launched an innovative clean energy marketplace aimed at providing better financial and operational insights to support renewable energy transactions. - learn more

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        🌴🧑‍💻 Your Guide to LA Tech Week 2024

        🔦 Spotlight

        Happy Friday Los Angeles,

        As many of you know, LA Tech Week is right around the corner, kicking off next Monday October 14th bringing together founders, creatives, investors, and engineers for a week of immersive events, panels, and socials across the city. From blockchain and AI to biotech and design, LA Tech Week is a chance to dive into the ideas shaping today’s technology landscape.


        What to Look Forward To

        Insights from Visionary Leaders: Hear firsthand from industry trailblazers as they share stories, challenges, and key lessons from their experiences. Expect fresh perspectives on AI, venture capital, biotech, and the ethical questions around emerging technologies.

        Interactive Panels: This week isn’t about watching from the sidelines; it’s about engaging directly with the tech community. Participate in hands-on panels discussing everything from startup scaling to ethical AI, with honest insights from those actively shaping these fields.

        Networking Mixers & Social Events: Meet and connect with founders, VCs, developers, designers, and fellow techies across LA. Rooftop mixers, lunch meetups, and creative gatherings offer the perfect chance to spark ideas and collaborate.

        Plan your week with the daily lineup, organized by location for easy navigation:

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

        Enjoy LA Tech Week 2024!!


        🤝 Venture Deals

        LA Companies

        • Clout Kitchen, a Los Angeles and Manila based startup, has raised $4.45M in seed funding, co-led by a16z SPEEDRUN and Peak XV’s Surge, to develop AI-powered digital twins, which enables gaming creators to produce realistic virtual avatars for content and fan engagement. - learn more
        • MeWe, a privacy-focused social media platform, has raised an initial $6M in Series B funding led by McCourt Global to support Web3 integration and expand its decentralized network for 20 millions users. - learn more

          LA Venture Funds
          • EGB Capital participated in a $10M Series A funding round for MiLaboratories, which develops software that enables biologists to independently analyze complex genomic data, accelerating research and discovery in fields like drug development. - learn more
          • Crosscut Ventures participated in the $13.75M seed round for Airloom Energy, a company focused on developing airborne wind energy technology to harness high-altitude winds, with plans to accelerate a pilot project in Wyoming. - learn more
          • Overture VC participated in a $5.5M Seed funding round for Molg Inc., a company developing robotics and software for circular manufacturing, designed to disassemble electronics efficiently and recover valuable materials to reduce e-waste and support sustainable production. - learn more


            LA Exits

            • Options MD, a Los Angeles based telemedicine platform that provides care for people suffering from severe and treatment-resistant mental illness, is set to be acquired by Resilience Lab, an AI-driven provider focused on enhancing mental health care access. - learn more

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