Episode 122 | August 28, 2025 | 32:50
Every year the same hesitations come up when coaches talk to me about conferences. I won’t know anyone. It’s too expensive. I’m not far enough along. Philip Taylor, CPA, entrepreneur, and founder of FinCon, has heard every version of these, and he’s watched thousands of financial professionals push past them and walk out with relationships, clarity, and momentum they couldn’t have found online. In this conversation, Philip and I work through the five biggest reasons coaches avoid conferences, and why each one, once you flip it, becomes the reason to go.
Key Takeaways
| Choose conferences where the attendees share your mission. The people in the room are looking for someone who gets what they’re building. | |
| Join the conference’s online community before you go, so you walk in already recognizing a few faces. | |
| Volunteer at the event. It builds in networking before the conference starts and gives you a purpose beyond just attending. | |
| Treat the cost as an investment with a clear expected return, and decide what you want to walk away with before you book. | |
| Google can’t break down exactly how someone pulled off their strategy, but the person next to you at lunch can open their laptop and show you. | |
| Conferences pull you into CEO mode. A few days out of the daily grind gives you the big-picture perspective you lose when you’re deep in operations. | |
| If you feel like you’re not ready, find the other people who feel the same way. Those early connections often become the most valuable ones you make. |
If you listened to last week’s episode, Ep 156: How to Prepare for a Conference (So You Don’t Waste $4,000), you already have the strategy. This conversation is the mindset piece. Preparation only works once you decide to go, and most of what keeps coaches home isn’t a logistics problem. It’s fear wearing the costume of logic.
FinCon 2026 is coming up September 16 through 18 in Palm Springs, CA, and registration is open now (use code KELSA50 for $50 off). Whether you’re weighing FinCon specifically or any professional conference, this conversation applies.
Who Philip Taylor is
Philip Taylor is a CPA, writer, podcaster, entrepreneur, and the founder of FinCon, one of the largest conferences in the personal finance and financial media space. He also runs The Creator CPA, a firm specializing in accounting for content creators. Philip has been featured in The New York Times, The Washington Post, Forbes, and Fox Business.
Philip’s first conference and what it changed
Philip’s first self-chosen conference was a WordPress event around 2004. He went in nervous, not knowing anyone, but excited to connect with people who understood what he was trying to build.
“It was big on the knowledge end for me. I learned a ton,” Philip recalls. “And then a few relationships that I formed there, folks that I still know today and rely on, and can look back on and think about those early days of making that connection.”
“It validated me too. It was early on in my entrepreneurial career, and having gone to that event, now I felt I was a part of the tribe.” — Philip Taylor
The validation caught him off guard. Being in that room made him feel like part of the tribe, and that feeling pushed him to take his entrepreneurial ideas forward. It eventually led to the creation of FinCon.
Fear 1: “I won’t know anyone.”
Walking into a room full of strangers feels intimidating. Philip points out that if you chose the right conference, everyone there is on the same mission.
“They’re tired of talking to their spouse about it. They’re tired of talking to the colleagues who don’t get it, or their employees. They need someone to really riff off of. And so if it’s the right conference, you’re going there to meet people who are on the same mission, which is cool.”
“They’re tired of talking to their spouse about it. They need someone to really riff off of.” — Philip Taylor
His practical advice for getting past this fear comes down to arriving warm rather than cold. Join the conference’s online community beforehand, whether that’s the Facebook group or the Discord channel, so you start forming connections before you arrive. Bring someone if you can, a colleague or a team member, because one buddy baked in changes the whole experience. Reach out to the organizers and offer to volunteer, which puts you in front of speakers and other volunteers before sessions even start. And use the conference app, which often suggests who you should meet based on shared interests. FinCon’s app is already live for 2026.
Fear 2: “It’s too expensive.”
Philip doesn’t pretend the cost is small. Tickets, flights, hotels, and food add up. He reframes it as an investment.
“I do think you should see it as an investment, and it’s a tax deduction, says the CPA, so you can write it off. It’s an ordinary and necessary part of growing a business to go to an industry show, or to go to a show that’s going to move you forward in your journey.”
The key, he says, is going in with a clear mission.
“I am investing in this, but this is the goal for it to result in XYZ. Have that mission in mind as you go to the conference.” — Philip Taylor
For the budget-conscious, which describes most financial professionals, there are plenty of ways to bring the number down: sharing a room, splitting an Airbnb with colleagues, travel hacking with points, choosing conferences that run over a weekend, and asking organizers about scholarships or alternative payment options. The deeper point is the lifetime value of a single connection. Philip still relies on relationships from that first WordPress conference in 2004. One referral, one collaboration, or one idea that shifts your business can cover the whole trip and then some.
Fear 3: “I can just learn this online.”
It’s a fair point. Podcasts, YouTube, courses, and social media have made information more available than ever. Philip draws a distinction between consuming information and connecting with people.
“Context matters and depth matters. How deep can you go? How are the Q&A sessions at the conference?”
Google can’t break down exactly how someone implemented their strategy, but the person sitting next to you at lunch can.
Two things online learning struggles to replicate are timeliness and real-time problem solving. Conference speakers update their content at the last minute with the latest strategies, and the person sitting next to you at lunch can walk you through exactly how they implemented something, sometimes pulling up their laptop to show you. There’s also the forcing function of being physically present. A course saved for later is easy to ignore. The person across the table answering the exact question you’ve been stuck on is not.
Fear 4: “I don’t have time.”
For busy professionals, Philip argues this is the reason conferences matter more, not less.
“It’s sort of a forcing function to come to a conference, to finally pause, take a break from the grind that you’re doing, and check those ideas against other people.”
He describes a pattern most entrepreneurs recognize, getting so deep in the day-to-day work that there’s never a clear moment to step back and think strategically. “Sometimes I just get down in the work way too much, and I don’t necessarily have a time on my calendar where it’s okay, this is executive PT, let’s put that hat on and be the CEO for a couple of days. A good conference will kind of force you into that CEO role for a couple of days, which is nice.” For the time-strapped, conferences that run over a weekend or trips paired with family time keep the days away from feeling like a pure trade-off.
Fear 5: “I’m not ready yet.”
This is the sneakiest one, the feeling that you need more clients, more revenue, or more credibility before you deserve to show up. Philip flips it completely.
“If you’re not ready to go to an event, I guarantee there are other people going to this event that are in that same boat. And so your job should be to go find who those people are.”
“I guarantee there are other people going to this event that are in that same boat. Your job should be to go find who those people are.” — Philip Taylor
Those early connections, the ones you make with fellow beginners figuring things out alongside you, often become the most valuable. Philip started FinCon because he wanted that exact experience. “I wanted that moment for myself. I was having it online in forums a little bit, and I would do meetups, but until I had the first one, I really couldn’t have that.” Good conferences build this in. FinCon runs a first-timers orientation as the very first thing on the schedule, a chance to meet other newcomers, get coached by experienced attendees, and leave the room with a few people at your same level.
Why I still go
After nearly two decades of building a financial coaching practice, most of my career has been remote. Client calls, Zoom sessions with coaches, podcast episodes recorded from my home office. I love the work and I still do it every week. Working alone, even when you’re constantly connecting with people digitally, can feel isolating, and conferences fill that gap. That’s why I go. I go to connect with the humans behind this work, the ones who remind me why I do what I do.
FinCon 2026 is September 16 through 18 in Palm Springs, CA. Registration is open at fincon.com with code KELSA50 for $50 off. I’m speaking on “From Content to Clients: How to Build a Business Your Audience Actually Pays For,” and I’m hosting a happy hour for financial coaches, with details coming soon.
Why this matters for your practice
The decision to attend a conference is a business decision, and it tends to surface the same hesitation patterns your clients bring to their money decisions. This week, look at whether the thing keeping you home is a true logistics constraint or a story about not being far enough along, because the answer changes what you do next. If you go, decide in advance what one outcome would make the trip worth it, the same way you’d help a client define what a financial decision needs to produce to be worth the cost. Walking in with that clarity turns a conference from an expense into an investment you can actually measure.
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