Shiloh Johnson: Founder & CEO of ComplYant – Ep. 134

About Shiloh Johnson & ComplYant:

Shiloh Johnson is the founder and CEO of ComplYant, a digital tax assistant platform that’s raised over 10 million in funding to date.

Shiloh’s personal journey is incredible, which you’ll soon find out, but the upshot is this: in her time as CPA, she noticed that many—most?—small business owners were making the same mistakes. 

She soon realized that there was a gap in the market and got to work building a platform to help business owners such as myself be a little less stupid. Ok, the stupidity part just applies to me, but everyone could use a little help.

This episode is great for anyone who’s thinking about starting a business or bringing an idea into the world. 

Full Unedited Audio Conversation:

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2:35 – “I have never believed in rules. My life is an example of that. I think those are just, rules are more like guidelines and you find ways to make things fit into what you need them to be. You can’t exclude yourself from the possibility of trying something because you don’t fit. Of course I don’t fit. I’ve never fit and I’m still doing it. Come join me.” 

Our Education System Is Terrible

*5:36 – “I think our education system is terrible. That’s probably why so few people know about it. I have so many thoughts about education reform, goodness. I certainly hate the fact – so tax code in general is written for small businesses. It’s written in to promote and support small businesses. It’s also written, the most code is written in favor of small business. But small business understands it the least. And I was just like, ‘Oh, I could do something here. This is a gap. I could fill it.’ And so hence how the product came to be. But I certainly feel like there are a lot of areas in general that we just don’t have practical knowledge around.” 

How NOT To Do Your Taxes

*6:40 – (Ross) “Well, I’ll tell you what you do. You get through a year, you just barely cover your bills. And then it comes April, and then you have a giant number that you owe and then you panic about, why didn’t I save any of that money?” 

(Shiloh)  “That sounds exactly like every small business owner I have ever met.”

(Ross) “And then you get a notification that you were supposed to renew your business tax license and you haven’t. And it’s two years past due, and then you get a bill. And then that bill says you owe just $2,000. No big deal, just a light penalty, and then you panic some more. I mean, that’s been my experience.” 

(Shiloh) “You and everyone else. Certainly the problem we set out to solve.”

7:39 – (Ross) “It’s no secret that we just don’t learn, certainly in America, any of the basics of the fundamentals of what becomes the most important thing in your entire life. You don’t learn basic accounting. You don’t learn how these tax systems work. You’re just on your own. And I mean, I think the idea is if you’re very cynical, that is just funneling you into getting a job and not really encouraging you to be entrepreneurial, because when you do that, you have to learn everything on your own. You have to, like you say, you could look at blogs, you can look at podcasts, you can read books, watch videos, do what you need. But all of that, you have to learn yourself. And unfortunately, most of it is trial and error. Most of it is you just try to make money, you try not to get in trouble and then something bad happens and then you wonder why and then learn a very painful lesson, right?” 

11:16 – “I know I did this for Technicolor or like Airmark or whatever, but who’s doing this for small businesses? And then you’re like, ‘Oh, yeah, no one. No one’s doing this.’ And the cost, right? You’d be shocked how many incentives corporations get to take advantage of because they just have the knowledge and they have the staff to help them sort of partake in all of the incentives, all of the tax cuts that small businesses don’t know about because they don’t have that same support. And I was like, ‘How can I productize and then make that available to like every small business I can find,’ which has been basically our mission.” 

A Solution For Small Business Owners Who Can’t Afford An Accountant 

*15:59 – “The way I think, my brain just, I think naturally I’m always thinking about ways to innovate or process change. I love process and I’m always thinking about process change which got me sparking the idea of: I’m getting all these clients coming to me with these crazy issues. If I could get them much earlier and help them so that they don’t get to this point – I can’t help everyone, how do I help the masses? Tech! Okay, let’s productize this so we can get to a lot of people, get them day one then help them sort of along the path until they can get to a really qualified accountant.” 

27:24 – “The first customer that says, like, ‘I am changed because you did this thing,’ or ‘you’ve helped me so much,’ or like, ‘I didn’t know what I was doing and I was really lost and like, I’m so thankful you’re doing this.’ You’re like, ‘Yes, yes, this is the win, this is why we’re doing this. That’s the North Star.’ Every webinar I do or every blog we’ve written and someone’s like, ‘Thanks, this is really helpful’ – it’s just that, it’s a little notch in that like, okay, we’re on the right path and it’s super exciting just to know that like I can contribute to the world something that has been my expertise that I can now give to someone else and make their life easier and as cheap as possible.” 

29:30 – “Another one is like not understanding that there is more than one type of tax. People think, just like to your point earlier, like income tax or TurboTax is the only thing I need to worry about. There are actually ten types of business tax and every single one of those things are very expensive if you don’t comply within range. And so not understanding that I think has been the biggest thing.”

30:10 – “The other one that’s super common: people don’t close their businesses down. So let’s say like you operate for a year, it’s trash, it doesn’t go well. You’re like, ‘I’m done with this. No more hair weaving company. Let’s let it go.’ They just walk away and they don’t do anything. And you actually need to tell the state you’re done. You need to tell the government, federal government, you’re done. You tell the city that you’re done. Because if you don’t tell them, they assume that it’s still open and they keep sending you notices and they want you to keep paying.” 

Can you negotiate with the IRS?

*32:20 – “People will say like, ‘Well, I got this bill. I have to figure out how to pay it.’ No tax bill is written in stone. I don’t care. No tax bill is written in stone. Everything can be negotiated. And a lot of times you can just do it yourself. Sometimes the naivete of ignorance works in your favor. You can call the city and say, ‘Actually, I didn’t know this, that I even needed to do this. And I don’t need, you know, is there a way we can negotiate this? Can I get a fee waiver? Can I get an interest waiver? Like, what are my options so that I can actually take care of it? I want to take care of it.’ Every government authority I’ve ever dealt with, they love the person that just wants to fix it. Even if all they can give is $0.02 a month, they will take $0.02 a month. Because you’re trying to be forthright.”

37:21 – “We literally teach entire webinars around tax anxiety and financial anxiety. I think that, aside from just sort of the lack of information, it’s almost like inbred in our culture, like our American culture is fear around money because we’re such like a financial behemoth and we participate in this competitive environment around money all the time. It’s always happening…We don’t talk about money in public spaces. We’re very hush-hush. Families oftentimes don’t talk about money. Cultures oftentimes don’t talk about money. So I think if we can open up the conversation around what’s happening with the money and how it’s moving, like, ‘hey, I don’t make enough. What are my options? How can I do more?’ And create that conversation more and more.” 

50:01 – [On why there are so few Black women who are CEOs] “I almost don’t think it’s racial in the sense that it’s like: ‘you’re a minority, I don’t want you.’ It’s that ‘I don’t know what to do. So until you show me something else, I don’t know what to do with you versus this person. I know what to do with because this is what I’m familiar with.’ And so there takes a bit of like requalification from other parts that are saying, ‘Hey, that person is actually pretty dope and what they’re building is pretty dope. And so you should actually go do something with them.’ So in terms of like raising money, that hasn’t been as difficult. What has been difficult has been like the belief in my ability to actually run the company successfully because again, CEOs don’t look like me.”

53:17 – “Don’t quit. It is impossibly easy to just stop. And you’re tired and you hate it and you’re broke and you can’t see the light. But I promise you, it’s there. Just keep going. Even when it sucks, even when you don’t see any result and you haven’t sold anything or you don’t know, you hit a roadblock, just keep going. When you hit the roadblock, get creative. Don’t quit.” 

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