From Bootstrapping as a Solo Founder — Shiloh Johnson Talks About Building Her Tax Platform ComplYant

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.

Want to hear more episodes? Subscribe to Office Hours on Stitcher, Apple Podcasts, Spotify, iHeart Radio or wherever you get your podcasts.

Subscribe to our newsletter to catch every headline.

From AI to Layoffs, Here's Why College Grads No Longer Want Tech Jobs

Lon Harris
Lon Harris is a contributor to dot.LA. His work has also appeared on ScreenJunkies, RottenTomatoes and Inside Streaming.
From AI to Layoffs, Here's Why College Grads No Longer Want Tech Jobs
Evan Xie

A new report in Bloomberg suggests that younger workers and college graduates are moving away from tech as the preferred industry in which to embark on their careers. While big tech companies and startups once promised skilled young workers not just the opportunity to develop cutting-edge, exciting products, but also perks and – for the most talented and ambitious newcomers – a relatively reliable path to wealth. (Who could forget the tales of overnight Facebook millionaires that fueled the previous dot com explosion? There were even movies about it!)

Read moreShow less

New Study Reveals Which Forces Are Driving Electric Vehicle Adoption

David Shultz

David Shultz reports on clean technology and electric vehicles, among other industries, for dot.LA. His writing has appeared in The Atlantic, Outside, Nautilus and many other publications.

New Study Reveals Which Forces Are Driving Electric Vehicle Adoption
Photo by Jannes Glas on Unsplash

The state of California wants 100% of new passenger vehicles sales to be fully electric by 2035. Last year, the state hit a nation-leading 16%. That’s pretty good, but 84% is still a long way to go.

A new study, published Monday in Proceedings of the National Academy of Sciences, investigates which factors have been responsible for the rise in new EV sales nationally. The findings indicate that consumers are increasingly likely to choose an electric vehicle, and nearly all of the gains can be explained simply by improving technologies.

Read moreShow less

Colleen Wachob On Navigating Her Wellness Journey As An Entrepreneur

Decerry Donato

Decerry Donato is a reporter at dot.LA. Prior to that, she was an editorial fellow at the company. Decerry received her bachelor's degree in literary journalism from the University of California, Irvine. She continues to write stories to inform the community about issues or events that take place in the L.A. area. On the weekends, she can be found hiking in the Angeles National forest or sifting through racks at your local thrift store.

Colleen Wachob On Navigating Her Wellness Journey As An Entrepreneur
Courtesy of Behind Her Empire

On this episode of Behind Her Empire, mindbodygreen co-founder and co-CEO Colleen Wachob shares her perspective on managing stress and navigating self-worth as an entrepreneur and the importance of celebrating the wins in your business.

Read moreShow less