Jonathan Medows on Why the Right Clients Find You
Canopy Practice Success — Jonathan Medows
Canopy Practice Success — Jonathan Medows
Canopy Host (00:01) Welcome to another episode of Canopy Practice Success. I’m your host, and today on the podcast I’m excited to welcome Jonathan Medows, a New York based CPA widely known for his deep expertise in taxes for freelancers, creatives, clergy, and independent professionals.
Jonathan runs Medows CPA, a boutique firm that blends traditional accounting with modern financial planning, business guidance, and education-focused resources that help self-employed individuals thrive.
Thank you, Jonathan. Welcome.
Jonathan Medows (00:41) Thank you for having me today.
Canopy Host (00:42) I’m excited to dig in. I teased this a little bit before we hit record, but I love that you and your firm are focused on a very specific clientele. I’d love to hear your story there.
How did you identify that these are the people you wanted to work with? I know I threw in clergy at the end. It wasn’t in my script. It was something you mentioned as a fun clientele for you. Talk about how you got there, how you found these people, and whether there are others.
Jonathan Medows (01:15) I started my firm with one client. Like a lot of people, I advertised. Back in 2004 I used the internet to grow my practice. I used Craigslist, listed my credentials, and frankly, whoever emailed me, I responded.
After doing this for about two, three, four years, I started to notice which clients resonated with me. Clients who felt I added more value than not, and clients who, from an interpersonal perspective, I enjoyed working with.
I quickly noticed that I liked working with self-employed people. With self-employed people, you can always guide them to tweak the next year. Maybe I can help them find deductions for the past year, but I can certainly give them guidance for the following year. With people who work for someone else, essentially I’m just the umpire.
A lot of times they would owe money because they were wealthy people who didn’t have enough taken out for taxes, and they would shoot the messenger. I found with self-employed people, even when they owed, if I could find a way to reduce their liability a little bit, they were much more grateful. That resonated with me.
Perhaps because I was on the journey with them, developing my own business, their issues and their needs and their stresses resonated more with me. We’re on the same journey. I may be a few steps ahead, I may be a few steps behind, but we walk together.
Canopy Host (02:46) You’re able to relate because you were in the same position.
So you identified this attribute that you really liked. Talk to me about how that has impacted your business model, your operations, your pricing, even your marketing. I’m sure it has had a huge cascade.
Jonathan Medows (03:15) Absolutely. Most of my marketing material is targeted to the self-employed. Not everything, because there are certain tax changes that come out and I like to be timely. With the big, beautiful bill, there’s a new Trump account for children. That doesn’t necessarily target the self-employed, but self-employed people have kids. So I try to stay on target by writing to the self-employed.
For example, during COVID there was certain economic relief, and I wrote about it from the perspective of freelancers. I really tried to write from the lens of freelancers and small businesses. I morphed the practice into small businesses as well, which are essentially more successful freelancers if you think about it, because the owner still has the same issues.
Our writing and our marketing are geared toward them. Our pricing is geared toward them, because you have people at different levels of startup activity and you have to be price sensitive. Same with our offerings and services. I can tier up and tier down depending on what people need.
People who are price sensitive want a little more no-frills, and that’s okay. We can do that. People who are more successful or busier want more services, and we can add that as well. I’m not one size fits all. I try to be flexible with people and meet them where they are.
Canopy Host (04:33) Now you said a verb several times, and as a marketer my ear catches it. You said write. You’re writing.
I actually just pulled up your firm’s website. There are a lot of articles. You’re writing blogs a lot, yes?
Jonathan Medows (04:51) Blogs, tax articles, third party sites. Correct.
Canopy Host (04:55) This is so uncommon. It’s very rare that I come across an accountant who is writing content based on tax updates, or things that are just pertinent to your audience.
There are plenty of listeners who are thinking, “I don’t have time for that. What do you mean, write?” Where do you see the value in this? Because you obviously see a value.
Jonathan Medows (05:27) Part of what I do is education. I have a staff. Prior to speaking with you there was a bit of an issue, and I had to do some education. I spoke with my manager and said, please speak with our senior accountants. Of course you’re going to put it in our checklist. Of course you’re going to email them. But I want you to have the conversation, because we have to teach.
I’m constantly learning. My staff is constantly learning as well. I like to write because when I write and put these articles together, I learn the material better. So it’s a teaching exercise for myself.
Canopy Host (06:01) First and foremost, you see it that way. Have you also seen it positively impact you in terms of SEO and marketing, with the right people finding you because you’re becoming a voice on the internet on these topics?
Jonathan Medows (06:21) In our business there are two ways to get clients. Either you go to a marketing event and hand out cards, or you think about when people actually switch. Either they’re starting something new and they’re searching for people and they find me that way, or there’s an issue.
So I try to speak to people’s needs. I write for certain places, and some people just follow the articles. But a lot of times people are searching on exactly what I’m writing about, and it comes up for them.
I’m essentially a bit of a defensive person in the sense that I’m responding to a need they already have. That’s why they’re reading my article.
Canopy Host (06:58) You may be aware of this as well, but that’s also why AI responses in search will pull content like yours. The questions people are asking that you’re answering through your written content are rather specific.
A little background into marketing here, because I find this fascinating and I feel like not enough people understand the value of it. The more domain authority you create on your website by publishing content that’s helpful, that answers questions people actually ask, that Google or any other search engine pulls into an AI response, the more power your brand is given and the more likely people are to find you.
I wanted to highlight that because people are asking questions, especially as we’re seeing these AI responses happen, whether that’s in the search engine or directly within an LLM like ChatGPT or Gemini.
That builds a snowball effect. You’re putting out information that’s applicable, you’re deepening your expertise because you’ve niched to these specific people, and then people find you because of that expertise.
Jonathan Medows (08:42) There have been times when I search and I come across my own article.
Canopy Host (08:46) I love it. So you’re doing all of the right things, Jonathan.
Jonathan Medows (08:52) But it takes time, it takes effort, and it takes money. Most accountants can’t write to the degree that people will appreciate what you’re writing. So you need help. You need a copy editor. You have to invest in it. And it’s okay to get help. You don’t have to do everything yourself.
Canopy Host (09:04) Say that 10 times.
Jonathan Medows (09:11) I’m not a bad writer, but I need help. Writing an article that appeals to people, that’s readable, is very different from a technical argument sent to the IRS on a specific issue. It’s a different type of writing.
Canopy Host (09:13) I like that you call that out, because you have expertise that people want to understand. It’s not a bad thing that your expertise isn’t writing. Your expertise is accounting.
But you know that information, you have that passion for education, whether it’s for your clients or your staff, and you’re asking what the best way is to disseminate it. If you need help putting that in the form that’s most easily understood, you get that help. I love that.
So you found this commonality. You liked self-employed individuals. You talked about writing. Talk to me about your processes, the team you set up, and how finding that characteristic has impacted the way you’ve built your business.
Jonathan Medows (10:23) I’m looking for people who take responsibility for their work. I can teach, but I’m looking for people who will own their work and put the hours in. It’s not a nine to five job. If I find that and they have the technical background, that’s great.
What we try to do is take repetitive, similar work, because then I can identify patterns and teach people how to do things. For example, if I’m dealing with a lot of freelance workers in New York City, aside from where we report the freelance income, there are very specific New York City issues tied to these people. That lets me create checklists and teach people. The art of repetition brings expertise.
I encourage people to do a little research on their own. As I was telling someone earlier today, I need people to reach, not to jump. When you feel like you’re jumping, call me. But I’m not going to spoon feed it to you after a while. Initially I will, of course. After that, I need you to do some research and then come speak to me. I try to treat people like adults.
That said, we double check all the work. And if there’s higher risk, we assign it to more senior people. I do have to keep that in mind. We need self-starting people who take responsibility. Unfortunately that sometimes means weekends, sometimes it means nights. That’s just the nature of being responsible.
Canopy Host (11:38) Something you’re not explicitly saying that’s worth calling out is the word delegating. When you delegate, and I love that you mentioned checklists, you don’t need to delegate something to someone who’s equally as skilled as you.
Jonathan Medows (12:10) Absolutely not. With that in mind, I actually developed our own workflow where I can route different types of tax returns at various stages through our offices.
Preparation for certain types of tax returns automatically goes to team A. Other types go to team B based on risk. They’ll automatically go to the appropriate level of supervision. I’ll sort out the reviewing sometimes, because myself and my managers know who’s more risky and who’s less risky, and we’ll sort it out.
Canopy Host (12:45) Do you have a rubric of sorts, or is it pretty subjective, more gut feel?
Jonathan Medows (12:51) With certain types of tax issues, we know we have to delegate. With certain clients, we just know they’re more sophisticated. It’s also knowing your clients. You do have to know your clients after a while.
But I have a very structured workflow, meaning I have software that manages the workflow in my organization from beginning to end. I’m constantly tweaking this. In April I’m already writing down the issues I see for next year. Always reviewing, always tweaking, because you can always improve things.
Canopy Host (13:27) Is autophagy the word I’m looking for? When something is left alone, it automatically disintegrates into chaos. That’s the same thing with our workflows. You can’t set it up once and expect it to work well every single year.
You live in a world of change. Clients grow in their own regard, you gain new clients, your employees come in and out of the business, the technology around you changes and maybe you adopt something new. I love that you’ve highlighted that it’s something you’re already taking notes on.
Jonathan Medows (14:09) Absolutely. I’ll give an example. The IRS is going to eliminate the ability to send in checks for payments. I’m not sure exactly when. I got a notification from my insurance company about a webinar.
So first, I’m paying attention to education and watching other professionals speak. Second, I’m going to take that feedback. And third, we’re going to have to change our workflow and our communications to clients. Internal staff, then clients, and then our workflow, to make sure we meet this.
Canopy Host (14:39) Talk to me a little bit about the culture you’ve set up on your team to enable them to identify and surface similar things as well.
Jonathan Medows (14:51) For the most part, a lot of people have been with me for a while. We have two managers and four senior accountants. Essentially I manage the managers mostly, and the senior accountants.
People know if something is up, they should ask. I send them articles constantly, and they know to go up the chain of command and ask other people. Eventually it comes to me. I try to respect boundaries, but people have been working with me for five, six, seven, eight years. So I know their strengths and weaknesses.
Canopy Host (15:16) When you’re sending articles, what are some of your favorite sources and publications for your own personal education?
Jonathan Medows (15:30) CCH does a nice job. I have a subscription to that. I like CCH, and then Intuit sends out articles, and other publications send out emails. If I see something, I’ll forward it along. I go to CCH. I find they do it very, very thoroughly.
Canopy Host (15:35) As you look at a firm that might be looking to do what you have done, you said you identified these attributes of clients within the first couple of years.
Did you have to fire clients? Did you maintain those few who came on in your first few years as legacy clients? How did you make the transition?
Jonathan Medows (16:22) It’s a little bit of both. Sometimes clients fire themselves. I don’t like to fire people because it’s confrontational and frankly it’s draining. On occasion we have to, don’t get me wrong. But that’s the exception more than my rule. That’s just my personality.
People eventually will get rid of themselves. You can make people go away. Either raise your fees or delegate them to someone else. I always feel it’s best that clients leave you rather than you fire them.
Canopy Host (16:38) I like that.
Jonathan Medows (16:52) That’s just my style. Other people disagree. I’m a nice guy, so perhaps that’s it.
Canopy Host (16:58) I think that’s an important call, because I’ve been hearing the phrase “firing your clients” for several years now. The concept being, don’t be afraid to do some of the things you’re saying. Raise your price. Change the qualifications for the types of people you want to work with.
But I like that you’re calling this out, because I do think it’s a mental shift. No, I’m going to raise my price. I’m not fearful of a conversation I have to have with my client. They’re a human with the ability to make a choice. Whether they choose me or not is fine. But I know what I’m choosing and what’s going to be best for my business, and I’m going to move forward that way.
Jonathan Medows (17:45) You don’t have to be obnoxious when you do it. Try to do it in a professional way. If you’re charging someone $1,000 and raising them to $10,000, that’s obnoxious. If you’re charging them $1,000 and raising them to $1,500, or even $1,800 or $2,000, whatever it is, that’s fine. Try to be nice. It’s difficult. You’re dealing with people, you’re dealing with personalities.
The other thing I’d recommend is have other people do this for you. If this isn’t something you’re comfortable with, get help. I’ll give an example. AR. I don’t like it. It stresses me out. It’s money. I have someone helping me do it.
If you don’t like to do certain things, there’s nothing wrong with getting people to help you and you being Mr. or Ms. Nice Guy. That’s fine too. It has to get done.
Canopy Host (18:28) I came across a concept a while ago that applies here with you delegating something you don’t like, something that stresses you out. Many people in business think they need to strengthen their weaknesses. I heard ages ago the concept of, no, strengthen your strengths. Focus on your strengths and make sure you build a team that’s complementary to you.
That’s such a great example. Jonathan’s strength is not AR. It stresses you out. So have someone else on the team do that. Don’t worry about something being your weakness. Lean into your strengths and let everyone on your team do the same.
Jonathan Medows (19:20) A friend of mine years ago told me I need to be grandpa a little bit. You’ve got to be the nice guy. That’s okay. You’ve got to know the roles at times. It’s a team effort. As you said, people are complementary. And don’t be embarrassed to ask for help.
I think most professionals in the accounting arena feel they have to do everything themselves. Maybe some of it’s financial. I understand money. You don’t have the money to do things at certain times. I get it. Believe me, I literally cleaned the men’s room when I first started. I get it.
But as you grow, I’m a bigger fan of getting a junior accountant right away and administrative staff, good admins, to free you up. You’re new as a partner. You’re the rainmaker.
If you want a better client base, that means you have to be nicer and more sophisticated. So you have to work on that. If being bogged down in the minutiae of admin, booking appointments, AR, and all that is going to wear you down, you’re not going to be successful. You have to invest in your business. Most people make this mistake.
Canopy Host (20:18) I hear these mistakes being made all the time. I also beat the drum that this isn’t an accountant’s issue. It’s an entrepreneur’s issue. By nature of being an entrepreneur, though your expertise is in accounting, it’s not that you’re plagued with this because you’re in accounting. It’s a natural thing when becoming an entrepreneur.
The business you’re starting is your baby in a way. It’s scary to think, how can I delegate something to someone? Will they do as good of a job? I think that’s very human in general.
But when you have this mental shift, I think it’s easier to hire. To see, okay, what do I need to make up for? I know what I like to do. I know my strengths. What should I be looking for in someone else? It’s not about trying to find another you. Don’t ever try to find another you. Find a Mary, a John, a Philip, people who will round out the business.
Jonathan Medows (21:36) You have to invest time and money to make that successful. You can’t have someone come in and hit the ground knowing everything you do.
Canopy Host (21:41) Right. And you’ve hired, you started your firm in 2004 and you’re now at 15 people. So you’ve hired 14, maybe a few more in there, people have come and gone.
What are some of your biggest learnings in the hiring process as you’re evaluating someone? Do you have questions you really like to ask?
Jonathan Medows (22:10) The first thing I need to see is whether they have technical expertise, or whether they don’t have the expertise yet but they have a foundation. I’m looking for people who have a strong work ethic. That’s very important.
Canopy Host (22:22) How do you evaluate that?
Jonathan Medows (22:24) I’ll ask them about challenges they’ve faced. I’ll ask them about the hours they’ve put in at their job. And I sometimes get a sixth sense from people after a while.
Canopy Host (22:32) Anything else you’ve liked or found when looking for individuals?
Jonathan Medows (22:38) Certain headhunting firms after a while, certain channels, certain schools. I’ve had luck with certain schools. I know if I hire people from certain schools, they tend to do well. Not everyone, obviously.
I also like to hire siblings. In the past I’ve had siblings work for me, and I’m having it again. I like it because I find a culture of accountability.
Canopy Host (23:02) Just by nature of having someone there. Interesting.
Jonathan Medows (23:05) Yes. I know some firms don’t like it. I find it works very well.
Canopy Host (23:13) It’s funny you say that, because in my career I’ve had instances where I’ve tried to refer my husband to a position that opened at a company I’m at, and it’s never worked out. There’s always this worry of nepotism. Even in other job applications I’ve filled out, that’s a common question I come across, especially with a large company. Are you related to anybody?
Jonathan Medows (23:37) It doesn’t faze me. There’s a culture of accountability that I like.
Canopy Host (23:45) I’m thinking, I’m going to see this person at Sunday dinner. I better step up my game. Interesting.
Jonathan Medows (23:53) It works for me. Again, it may not work for other people. I just don’t want to be dismissive of it.
Canopy Host (23:56) I love it. As we round out our conversation, I have a couple of rapid fire questions for you.
Do you have a favorite tax deduction or tax hack that you feel like other firms miss?
Jonathan Medows (24:17) In New York, a lot of people work from home. A lot of firms are reticent to take a home office deduction, but in New York City it’s very common for people to work at home. So I like that.
As a corollary, I’ll tell people to tone down travel and meals, because I find they tend to be abused, and people with heavy travel and meals tend to be audited more likely than not. Again, I’m New York-centric, so there’s also the New York State Department of Taxation and Finance, so I’m sensitive to that.
Even if you win an audit, and we do win audits of course, the stress of going through it is rather unpleasant.
Canopy Host (24:52) It’s like, let’s just avoid it entirely if we can.
Jonathan Medows (24:55) If it’s possible. If it’s legit, it’s legit. But I’ll make sure. If I think something’s excessive, I’ll ask.
Canopy Host (25:00) What’s one piece of advice you’d give every first time self-employed person?
Jonathan Medows (25:07) You’re going to go backwards to go forward. I went backwards. You’re going to make less money initially. You have to be prepared for it. Transition into it.
I wasn’t able to do this because I was in graduate school. I started my CPA and I have other degrees, and I had very modest expectations in terms of money.
Canopy Host (25:09) Just giving yourself the room to ramp your business.
Jonathan Medows (25:34) I had three jobs at one point when I started, because I needed it. As we built the practice, I ditched the other part-time jobs.
Canopy Host (25:36) Last one. What’s one tool you think every freelancer should be using? Or if we want to broaden it, every self-employed individual.
Jonathan Medows (25:55) I think communicating with clients is the main thing. WhatsApp, email, text messages. But have a number separate from your personal one.
Be responsive, but you don’t have to be a slave to these devices. I’m guilty of it myself at times. I’m pretty responsive to people. The main thing in starting a business is communication. People like it. Be responsive, but if people are abusing it, slow it down.
Canopy Host (26:27) I love that you said have a separate number. And if you can put it in a secure channel, whether it’s WhatsApp or Slack or something.
Jonathan Medows (26:42) Whatever floats your boat. For me, I use WhatsApp now because I have a lot of international clients.
Canopy Host (26:43) Well, Jonathan, thank you so much. It was so fun to dig into your business and get into the nitty-gritty with you. I love that you’ve found writing and marketing. As a marketer myself, I’m passionate about those things and I know they benefit a business, so it’s really fun to find an accountant who does that as well.
Jonathan Medows (27:12) Thank you so much for having me.
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By: Chrissy Rutledge
Chrissy is the Social Media & Content Marketing Specialist at Canopy.
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