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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Fuel Innovation: 7 Unforgettable Team Building Experiences in LA
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In today's competitive business landscape, team building activities have emerged as a crucial tool for fostering a positive work environment, enhancing productivity, and crucially, improving employee retention. Studies have shown that such activities help employees feel valued, with one report indicating that 93% of those who felt appreciated were more motivated at work. Importantly, team building events may improve retention rates, as employees who feel connected to their colleagues and company culture are more likely to stay long-term. With these benefits in mind, let's explore some of the most engaging and effective team building activities available in Los Angeles.


Image Source: Modern Luxury Angelino

Pickleball is a fantastic team bonding activity because of the easy-to-grasp rules and gentle pace make it perfect for everyone, regardless of age or fitness level. The game thrives on communication and teamwork, as players must collaborate and strategize to outplay their opponents, boosting team cohesion. Plus, the lively, fast-paced action sparks friendly competition and laughter, creating a fun and spirited atmosphere that brings everyone closer together. Los Angeles boasts numerous pickleball courts that are easy to rent if you have your own equipment. If you need additional assistance organizing your pickleball outing, there are plenty of full-service companies ready to handle every detail for you.

Resources: Pickle Pop, Corporate Pickle

Escape Room

Image Source: The Escape Game

Escape rooms are a great way to build camaraderie. They require participants to work together, combining their problem-solving skills and creativity to overcome challenges and puzzles. The immersive and time-sensitive nature of escape rooms fosters collaboration and communication. Additionally, the shared experience of tackling complex tasks and reaching a common goal helps build trust and foster positive emotions among colleagues.

Resources: The Escape Game, 60Out

Day Trip to Catalina Island

Image Source: Love Catalina

Catalina Island is a perfect day trip for a team because it provides a break from the usual work environment, allowing team members to relax and connect in a new setting. Shared experiences during the trip, such as exploring new places and participating in fun activities, help build stronger relationships and foster a sense of camaraderie. There are numerous team-building activities such as an arboreal obstacle course, an island tour, scavenger hunts and more.

Resources: Catalina Island Group Activities

Top Golf

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Topgolf is an excellent team building event because it provides an inclusive, relaxed atmosphere that accommodates players of all skill levels, fostering personal connections and improving team morale. The unique blend of competition and entertainment creates an ideal setting for building trust, enhancing communication, and revealing hidden skills among team members. Additionally, Topgolf offers structured team building packages with guided activities, discussion prompts, and lessons on culture, change, collaboration, and strategy, making it a versatile and effective platform for strengthening relationships and boosting overall team performance.

Resources: Topgolf El Segundo

SoFi Stadium Tour

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A SoFi Stadium tour offers a unique, behind-the-scenes experience of one of the world's most advanced sports venues, allowing team members to explore exclusive areas like premium suites, team locker rooms, and the player tunnel together. The tour provides a shared, memorable experience that can foster camaraderie and spark conversations among team members, regardless of their interest in sports. Additionally, the stadium's state-of-the-art features and impressive architecture can inspire creativity and innovation, while the group setting encourages interaction and collaboration, making it an engaging and enjoyable activity for teams of various sizes and backgrounds

Resources: SoFi Stadium Group Tours

Corporate Volunteering

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Volunteer work serves as an excellent team building activity by uniting employees around a shared, meaningful cause, fostering a sense of purpose and collective accomplishment. It provides opportunities for team members to collaborate in new ways, often revealing hidden strengths and leadership qualities that may not be apparent in the regular work environment. Additionally, engaging in community service can boost morale, enhance the company's reputation, and instill a sense of pride among employees, leading to improved workplace relationships and increased job satisfaction.

Resources: Habitat for Humanity, L.A. Works, VolunteerMatch

Corporate Improv Sessions

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A corporate improv class encourages spontaneity, creativity, and quick thinking, skills that are valuable in the workplace. It promotes active listening and collaboration, as participants must work together to create scenes and respond to unexpected situations, fostering better communication and trust among team members. Additionally, the playful and often humorous nature of improv helps break down barriers, reduces stress, and creates a shared positive experience that can improve team morale and cohesion long after the event.

Resources: Improv-LA, Groundlings, Improv for the People

🎬 Paramount and Skydance Are Back On
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Happy Friday Los Angeles! Hope you all had a fantastic Fourth!!

🔦 Spotlight

Paramount and Skydance Media have rekindled talks to merge after negotiations abruptly halted in June. The proposed deal, contingent on approval from Paramount’s board, aims to combine Paramount’s extensive media holdings—including CBS, MTV, and Nickelodeon—with Skydance’s film expertise showcased in hits like "Top Gun: Maverick." This merger signals a potential transformation in the media landscape, positioning the new entity to compete more effectively amid challenges from streaming services and the decline of traditional cable TV.

Led by Shari Redstone, Paramount’s controlling shareholder via National Amusements, the deal represents a pivot towards revitalizing Paramount’s strategic direction amidst financial struggles and shareholder concerns. The involvement of major investors like RedBird Capital Partners and David Ellison underscores the financial backing aimed at stabilizing Paramount’s operations and addressing its $14 billion debt burden. Importantly, the agreement includes provisions to protect National Amusements from potential legal challenges, addressing previous hurdles that stalled earlier negotiations.

The deal also includes a 45-day period for Paramount to explore alternative offers, highlighting continued interest from other potential buyers like Barry Diller’s IAC and media executive Edgar Bronfman Jr. This flurry of activity underscores the significant stakeholders’ interest in Paramount’s future and its potential as a key player in a rapidly evolving media industry.

🤝 Venture Deals

LA Companies

  • Sidecar Health, a startup that offers personalized health insurance plans to businesses that allow members to see any doctor and pay directly at the time of service, raised a $165M Series D led by Koch Disruptive Technologies. - learn more

LA Venture Funds

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