In this episode of the Union Podcast, wedding planner Jamie Wolfer shares a live Q&A from a mastermind call, offering practical guidance for newcomers to the wedding planning industry. Jamie opens with a brief personal intro, emphasizing his journey to a six‑figure business and his mission to demystify the trade. He then tackles a series of listener questions: 1. Networking anxiety – Jamie recommends using Instagram DMs and professional Facebook groups as a “happy medium” between cold emails and in‑person handshakes, encouraging planners to compliment vendors, propose styled shoots, and build relationships gradually. 2. Contract management – He recounts his early habit of printing paper binders, then explains why he switched to Honeybook for digital contracts, proposals, and client communication, highlighting its customization features. 3. Affordable legal contracts – Jamie promotes Legally Set, an attorney‑crafted, industry‑specific contract library that is budget‑friendly, and also notes Honeybook’s built‑in templates as a stop‑gap. 4. Bookkeeping & tax compliance – He advises QuickBooks Self‑Employed for mileage tracking and expense categorization, stresses the importance of a separate business checking account, and reassures listeners that following these basics will keep them out of legal trouble. 5. Setting realistic business goals – Jamie discusses realistic event volume (15‑20 weddings in year 1), the need to calculate hourly rates, and the value of a pragmatic, “snowball” approach to revenue and debt repayment. 6. Automation of payments – He demonstrates how Honeybook can send automated past‑due notices, reducing awkward conversations. 7. Sponsor offers – Throughout, Jamie shares discount codes for Honeybook, Legally Set, and his own services. The episode blends conversational storytelling with actionable, step‑by‑step advice, aiming to equip new planners with the mindset, tools, and confidence to grow their businesses without overwhelm.
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Hi and welcome to Union Podcast.
My name is Jamie Wolfer and I'm a wedding planner who absolutely loves to share how I got started and scale my business to above six figures in this amazing and occasionally extremely competitive industry. In this podcast I share the tech tactics, mindset and mistakes that got me to where I am today. No gatekeeping, no cloak and dagger, just full disclosure and a little humor along the way. So whether you're a planner or a solopreneur, my goal is for you to be a better business person than I ever could have been and support you on this journey.
I let's dive into this week's episode.
Today's episode is one of my favorite things in the entire world and that is a live Q and A from one of our union mastermind calls.
I know you're going to love it. Take a listen. Advice for networking without it being so anxiety sweat provoking Brittany, I love you so much. Literally I get anxious, my hands get sweaty, and then the idea of shaking hands with my clammy wet hands is a nightmare fuel because yuck. For obvious reasons I considered cold emails, but I've heard bad things from vendors I about their experience with cold emails. So I don't want to leave negative first impressions. What do you suggest for the networking anxiety and your opinion on cold calls slash emails and how to go about them? So I actually I like cold DMS way better personally because I feel like reaching out to someone on Instagram being like, hey, I love your vibe, I love your style. I what this last style shoot that you did, nuts like this. The gallery for this wedding looks so cool. I'm an up and coming planner. I would really like to plan a styled shoot or whatever that happens to be and then just go fangirl on different people's pages and start developing a relationship that way, you know, show up how you wish vendors would show up for you and if you can find others, other vendors that are kind of on that smaller scale, that's a great idea. If you could find someone who's a little bit larger and maybe they can take on even more of like advice in your area, that's fantastic. So I prefer social media marketing, like networking, sorry, including Facebook, like Facebook groups is a great place to get into, especially if it's a professionals only because then you can go in and you can ask questions because obviously we have these calls and they're fantastic if I just say so myself. But sometimes you have logistical questions about your area. So that's how I would recommend doing it because Then you can still kind of cold message people, but you can develop and build relationships. That's not a cold email or a cold call because I've received those kinds of emails in the past. And like, I mean, I like your professionalism. That's great. I wouldn't say I had a negative reaction to it, but I can also understand, I think that social media feels like the happy medium to me personally.
Yeah, I'm only mildly embarrassed to admit that in the beginning, I printed out every single piece of paper, every single contract. I took handwritten notes and created a binder for every single one of my wedding planning clients. Now in theory that sounds really cool.
And I thought I would look really.
Cool showing up to these meetings with these binders that are full of all of these contracts with handwritten notes. But let me tell you, the chaos that ensued when I tried to stay organized on my own and got over five events at a time. It was a nightmare. Enter Honeybook. I am telling you guys, Honeybook was literally exactly how my brain was processing wedding planning. But, but just in digital form. It's so easy to go in there and make any sort of customizations that you want. From adjusting your contracts to adjusting your packages, maintaining conversations back and forth that not only pop up in the app on the website, but also in your inbox as well. It's a great way to stay organized.
So get out of the paper and get onto the Digital.
Head to wolferenco.com HB and use code Union at checkout to get the best deal. We interrupt this podcast because there is something extremely special that I wanna share with you guys. I don't know about, but for the last who knows how many years I have been using a frankensteined, googled, copied and pasted contract. And while that is extremely embarrassing to admit to all of our listeners, I know that there are people out there who feel the same as I do. And there were a couple of things that kept me from actually getting an attorney drafted contract. Actually, no, there was one thing. It was so expensive and it seemed so out of reach. That's when I learned about Legally Set. You see, Coon Bee with Legally Set has created industry specific contracts for people like you and me working in the wedding industry. They're easy to customize, they're drafted by an actual attorney and not googled. Can you imagine that? And last but not least, they are so extremely affordable. So if you were like me and maybe using a less than appropriate and or legal contract, it's time to step up your game. You have no more excuses. Head on over to theunionpodcast.com legal legally set to check them out. Use code union for 20 off your contracts.
Okay. Actual logistics of running a business pertaining to taxes, accounting, bookkeeping, etc. I'm an extremely detail oriented person, so I keep getting hung up on these tiny little things and I'm kind of scared when it comes to the legal slash tax side of it because I don't want to go to prison. Are we the same person? I literally have said I don't want the IRS to arrest me. Like deep fear that I'm like, I'm going to go to prison because I didn't file this receipt correctly. Please help for reference. I'm in West Virginia, so I know state laws can be different, but I just kind of but I just need a reference point to know where to start. Also, I'm stuck at the contract stage. I don't want to officially book anyone without a contract, but can't afford to invest in proper legal contract. Anything I could do in the meantime to keep me covered. So obviously I'll answer the first part first. I would think that QuickBooks would be a really good solution for you if you don't already have it because it'll walk you through. Especially if you have QuickBooks self employed. You have the app on your phone, it'll track your driving and then you could say this was for work, this was for personal, and so you can actually track your mileage. That's what I did in the very beginning. It was very, very smart. Especially when you're traveling an hour and a half, two hours to weddings each way. You really want to make sure you're tracking that mileage so you can pay yourself for that accordingly or then get a tax disc refund. Clearly I'm really good at this, but that kept us really neat and tidy for a long time because we didn't officially hire a CPA or a bookkeeper until we reached a certain point of income. So that's kind of the place that you're at where you're just like, I can't afford to go professional, but I want to make sure my hiney is covered. So I would say QuickBooks, I'd go with that. QuickBooks self employed get the app on your phone because then you can also go through and categorize things. I would also make sure that you are doing this in a separate banking account. That's one of the best biggest reasons that small business owners can kind of get really stuck is you just don't was that Amazon purchased for work? Was it for home? Just complicates things a lot. So if you can, especially if they're very cheap or free to open up, I would recommend getting a business checking. Get a debit card to go with that and have all of your finances run through there, everything. So even if like you go out to coffee with a client, you could put on that card. So that's the cleanest way of handling it. Until you get to the point where you can afford a professional. And I don't think you'll go to prison, especially if you do those two things, you should really be okay. I would caution not putting too many things on the business. You know, we've all seen that scene from Schitt's Creek. Whether you've actually seen the show or not where David talks about the write off people. I don't know. It's a write off. Who pays for it? The write off people, we. So just if it's business adjacent. Yeah, that's it could go on that card. Now for the second part of your question. Also, I'm stuck at the contract stage. I don't want to officially book anyone without a contract, but I can't afford to invest in proper legal contract. Anything I could do in the meantime to keep me covered, I would suggest. Honestly, Honeybook is a great stepping stone for contracts. If you don't have Honeybook already, I think we have a discount code with them that makes it a lot more affordable. Rebecca, if you could find that and drop that in the chat just so you could see what the discount is and see how helpful that might be because they have contracts preloaded. So what you can do is you can technically go in there and change them. They also have proposals done for you, they have questionnaires, they make it there. It's all templates. So I would assume, of course this is not legal advice. I would assume that they wouldn't be putting out contracts that you can't use. However, the legally set contract is specifically designated for wedding planners, for event planners. So it has real specific language in there that I highly recommend. But if you're not at that stage, yeah, let's not be spending money on that. Let's get you in a Honeybook, which is actually like a really good client relationship interface. You won't double book. You don't have to follow up with clients for. With customers to be like, hey, you owe me money. That's my. I hate it. I hate sending that email of like, hey, your payments due?
Hey, Your payments past due.
So to have it automated and to have it be a very clear automated message saved the enneagram 3 in me because I absolutely hated being like, so this is awkward, but I can't meet with you until you pay me. Sorry. So. Oh, is that the current one? $1 for the first eight months. Yeah, it's kind of hard to argue with that one for sure. And they also offer a free trial, so if you want to, you can just sign up for a free trial and test it out for seven days, see if you like it. I find it to be kind of like a business in a box. It's really nice because it has all of those things for you. But then you could change the hex codes so your, your colors are on point. You can add in your logo, you can change the fonts around. So that's, that's where I would start with that one. Specifically, what should my realistic goals be? I have high expectations for myself and want to know as a new business owner where I should actually be with my expectations. Well, I don't know what your goals are and what your expectations could be or should be. That's like I adore you. I just don't know how to answer that question. I would think that I would not expect to be profitable for a while. I think a lot of people want to replace their full time job immediately and it's just not possible. So either you take a pay cut or you keep working your full time job. Which for me, I actually didn't do much wedding planning during the day, even though I was a stay at home mom at that point. I did most of my meetings after my husband got home because I had a Todd. Like I just couldn't. And most of my clients work nine to fives anyways. So it does kind of put you in a position where if you are working a 9 to 5, you are kind of in a great spot because it gives you time to build up your business. But you're going to go through a season of long days, long hours. You can of course manage what you book and manage how many people you see, etc. How many weekends you work. But there is going to need to be probably some of that overlap unless you're married and your spouse has, oh gosh, smacking my microphone. Your spouse has enough to cover you in that interim. So that's where we were at. So that's really fortunate for us. So as far as your expectations, I think a lot of people expect to make a lot of money real Quick. And you can get good money if you throw yourself at it. And if you throw money in advertising or go to an expo, you can ratchet it up pretty quickly. But I think practically speaking, maybe the first year, 15 to 20 events, I mean, most people go a lot slower than that. So this is not like a gold standard, right? So if you're like, I did four, great, you're going at the pace that your life is allowing you to go at. But I wouldn't anticipate hitting like 30 to 50 in the first two years. So adjust how much income you think you're going to make off of that based on what you're charging. Obviously, if you've gone through the pricing section, the pricing module of the course, we talk about what your hourly rate is. So if you look at that and you go, I can afford to live off of 20, 20 weddings this year. And then you're like, I'm going to do that. So I actually kind of like to reverse engineer this. I was a single mom for a really long time. Not really long time. For like five years. I felt like forever. So budgeting for us wasn't like a like, sure, let's just test it out, see if we know. It was like, I had to. So you look at what your expenses are, look at what you have to cover, and then can I make enough money to cover those things? So I like keeping expectations really realistic and goals really achievable, because then when you hit them, you feel like a boss. Love them or hate them. Dave Ramsey has this idea of the snowball method, where if you pay off a small loan or a small credit card debt, you get this feeling of elation, of like, oh, my goodness, I can't believe I just conquered that. And then it starts snowballing and getting bigger and bigger. So as far as expectations and goals, keep them practical, keep them logical. Check your hourly rate and then calculate out, this is how much time I think I'm going to spend on this wedding and that the pricing module is going to be your best friend on this one specifically. So that's what I would say, I think. I think dreaming and getting excited is so fun. I think being practical will actually behoove you in the long run.
That's all we have for this week's episode, guys. If you enjoyed it, do me a favor, screenshot that episode and share it on socials. Tag me in it. I would love to see Wolfer and Co on Instagram. Let me know if you're enjoying it. You can also let me know if you didn't enjoy it, but I'm probably.
Not going to reassure that one.
I hope you guys enjoy this week's episode, and we'll see you in the next one.
