How My Business Actually Got Off The Ground (After 2 Years of Struggle)

Want to get your business off the ground? Start hosting your own events to make it a reality! I'll show you how.

I've got to be honest with you...

From 2013 - 2015, my business was STRUGGLE. CENTRAL.

Some of you may know me in-person, and if you’ve ever had a coffee date or a Skype date with me, you’ll know that the first thing that I’ll tell you is that I am SURE that if you stay with your business for at least 2 years, you’ll end up creating something sustainable that will sustain you for as long as you want to be in business.

However, those first two years? THE FIRST TWO? Those are the hardest. It’s the time that you’re trying to figure out your message, you’re trying to understand the elusive “ideal client”, you’re trying to figure out what your clients want (and more importantly, what they want FROM YOU specifically)’s a struggle bus, for real.

I remember the first time I realized that I would either have to pay taxes or pay my rent, and I laid on the floor staring at the ceiling for two hours. I remember going on long walks with a neighbor, and constantly asking her why everything was SO up and down. Some days I had TOO much client work, some days I had no client work. Some days I was a superstar at getting work done, some days I refreshed my inbox 45 times an hour, praying that someone would email me to ask me to help them plan an event.

It was maddening. And time consuming. And I probably would have gone on for years like that, if I didn’t decide to take matters into my own hands. Instead of praying for clients, I knew I had to go out and get them.

However, the only way I really knew how to do that, was to ask a bunch of my friends how THEY were doing it. So I started a small mastermind group, with 10 ladies, in my house.


Here I was, thinking I was unique in the struggle of figuring out how to run my business. Instead, I realized that ALL business owners that I knew were working on their own challenges of outreach, marketing, sales, and client acquisition. Regardless of anything else, the power of hosting this event made me realize how powerful it is to have your own community of people you can tap into for help.

Want to know how to plan your own, super successful event for your biz? Grab my event planning cheat checklist below to get started!

At the end of that first dinner party I hosted, three or four women came up to me and asked if, next time, they could bring their roommate, or their sister-in-law. They wanted to help other people who had similar struggles, and weren’t able to organize the group themselves. So they asked me to be the organizer.

And herein lies the beginning of the end of my business-as-a-struggle-bus. This was my AH-HAH! moment. I realized that in order to get out and impress people, in order to get clients, I needed to showcase the work that I was doing. I needed people to understand how good of an event host I could be, and I needed them to tell their friends about it.

So, when I launched the Boss Lady Bash, and it sold out, I was scared to host it (since I never had done this before), but I knew deep down that it would raise my profile in the service-based business industry that I was trying to infiltrate.

And for real, for real? The first event that I hosted barely broke even. I went ALL out on the venue, the food, the cute little swag items. I got a bunch of people to sponsor it, and a bunch of other people to help volunteer at the event, and it still wasn’t profitable. It wasn’t until later that I realized that often, the power of events isn’t in the one event itself -- it’s in positioning yourself to be in a leadership role, as someone who knows what she’s talking about.

And it was SO worth it. In the matter of a year, I hosted 4 other events for my business, I booked myself out for 1:1 services, raised my rates, and was asked to speak 4 or 5 times that year. Even now, people have said to me and say “Wow, I didn’t realize you’ve only been in business since 2015. You came on the scene so quickly!”

(Actually, I’ve been in business since 2013, but no one knew who I was until 2015).

I have a good salary (more than what I was making in NYC), I get to travel internationally for work about 3 times a year, and I’ve been able to invest in my business to help it grow 20% in revenue each year. And there’s SO much more to do. Hosting that very first of many events has completely reshaped how I do business, and has led to an incredible transformation in how I host events, how I help my clients host events, and how I make events profitable every single time.

While my business isn’t perfect (seriously, if you think it is, we need to get on a Skype chat and I can show you my out-of-control living room/work space), I’ve been able to make more sales, meet more people, and find better communities since I’ve started hosting my own events. I’ve even had other companies and non-profits approach me to understand the methodology and content I use to get more engagement AND to get people to talk about the events with their friends, their families, and their co-workers.

To be honest, most people don’t get out of the struggle. They’re constantly going back and forth about their message, they never really quite understand who it is that they’re serving, and they stay stuck in the rut of their comfort zone...aka doing the things they know how to do, but never learning to do new things, which keeps their business at a standstill.

If you’re struggling with this whole “online business” thing, or you need to get more clients, or you need to get more QUALITY clients, then I highly recommend hosting your own live event.

To help you get started, I’ve created a fun event planning cheat sheet that will take you from content structure, to planning, to execution. It’s a pared-down version of the cheat sheet that I use to plan my events, so I hope you love it!

Are you ready to get started planning your own events? Download my event checklist (it's the one I use to kickstart all of my events)!

Lauren Caselli6 Comments