How to Know When It’s Time to Change Paths (Jess Bumsted from Root & Trellis and Book More Women)

Jess Bumsted shares her journey from booking agencies and major festivals to launching growth consulting firm Root & Trellis, along with her work advocating for diversity in live music through Book More Women.

Follow Jess Bumsted:

Website (Root & Trellis)

Website (Book More Women)

Also Available On:

Apple Podcasts

Spotify

Transcript:

Mike: Hey Jess, how are you?

Jess: I’m good. How are you?

Mike: I’m doing fantastic. We had a great conversation earlier, and I feel like every time we chat, it always gets me excited about what we do. I cannot wait to talk about your origin story because you have such an amazing background, coming from the music industry and then leading into the company that you have today.

I do want to start with asking you this question. Both you and I have seen so many people over the years — clients, colleagues, friends — who either did or didn’t reach the level they wanted in their careers.

Was there any particular attribute you noticed about the people who actually became successful and got where they wanted to go?

Jess: Yeah, I mean, I will say, for the music industry — and really any career that is demanding or adjacent to the spotlight — it’s kind of a requirement that you really want it, almost more than anything else. You have to be driven in a way that’s kind of endless.

And honestly, I think the people who succeed are able to look out for themselves over the company they’re working for. That’s something I see a lot of young people get tripped up on. They fall into traps where they think loyalty to the company is everything, but the people who do well are the ones constantly checking in with themselves and asking,
“Is this working for me? Is this worth the sacrifice?”

They make sure the scales are balanced between what they’re putting in and what they’re getting back, and they don’t let themselves burn out for no reward.

So I’d say it’s independent-minded people who can function inside a company or on their own, but who stay passion-driven and stick with it because they genuinely love it.

Mike: There’s definitely something to be said about complacency. That’s a big one.

If someone is happy where they are, that’s great — honestly, that can be rare. But for people who aren’t satisfied, it’s easy to get comfortable and just stay there because change is scary.

The people who are successful seem to be the ones who keep doing those check-ins. Even if they’re not unhappy, they’re always asking,
“Is this working for me? If not, what needs to change?”

Jess: Yeah, exactly. I’ve been in the agency world forever, and I think those kinds of jobs aren’t really set up for you to stay comfortable in one spot.

Assistant positions especially aren’t designed to be financially comfortable forever. They’re meant to push you. You either move up, or you move out.

You move up into the agent role and keep hitting numbers, because it is a sales job at the end of the day, or you move into another department or another path entirely.

One of my first bosses compared it to being a good agent. You can’t rely on one person to make your career happen. You have to advocate for yourself.

If you feel stuck, you don’t just sit there. You look around.
Who can help?
Who can I talk to?
How do I network?
How do I make this happen?

You hustle for yourself, not just for the company.
You do your job well, but you go the extra mile for your own career.

Mike: So you started out interning for a number of agencies. Did you know early on that this was going to be your path? Like, “I want to work in live events, I want to work in booking”?

Jess: Yeah… when I was in high school, I was always around music.
I played drums, I sang — I wasn’t very good at either of them, honestly — and I didn’t have the discipline to really get great at it. I loved hitting the drums, but I wasn’t practicing rudiments.

But I had friends who were amazing musicians, and I kept thinking,
“How can I still do this without being the one on stage?”

That’s when I started learning about how the music industry actually works. I went to a high school that focused on rock music, so I was around people playing shows and doing that whole world.

When I applied to college, I basically decided I was either going to go to trade school or go to a music industry program. I didn’t tell my parents that — I figured I’d only bring that up if I didn’t get into any music schools.

I only applied to a couple schools with music business programs. Drexel was one of them, I got in, and I went there for music business.

The first year you do both the tech and business tracks, and then you choose. I went business.

One of my professors was Eva from Fata Booking, so that’s how I met her.
Communion Music was another early job for me — that started as street teaming through school, and then turned into an internship.

From there I got connected to Fata, and eventually my first assistant job, because people knew each other.

That’s kind of how everything started.

Mike: So when you got into Drexel, specifically for the music business program, what did your parents say about that?

Jess: They were stoked, because it was a college.
They were like, “Awesome, great.”

At the end of the day, I still got a business degree, even though it was a specific track, so in their eyes I was secure. I wasn’t doing anything too crazy, and I wasn’t skipping education. So they were totally fine with it.

Mike: That’s great. It’s always interesting, especially with the music industry, because some people don’t realize how many different careers exist in it.

They think about artists, but they don’t always think about booking, live events, management, all the other sides of the industry. There’s a lot you can do, and it can lead to a lot of different paths.

Jess: Right, exactly.

Mike: So you worked with Eva, and Eva’s amazing — I’ve known her for years too.
Then you moved into a full-time position.

Can you talk about that time? It sounded like you were enjoying the work while you were interning, so what made you want to keep going down that path?

Jess: Yeah, I remember very clearly when I decided I wanted to work at a booking agency.

Most of my professors my first couple years were men, and then I remember we had a class about the live music world, just an intro to how everything works.

Eva walked in to do her section, and I remember thinking,
“Holy shit. This is it. This is what I want to do.”

She was just this badass woman who walked in and said,
“I’m a booking agent. This is what I do.”

And I was like, that’s it. That’s the job.

Working with her, even just a little bit, was awesome.
Working with Communion was great too.

One thing that’s kind of a theme in my career is that I’ve almost always come into situations where something new was being built.

Rarely have I walked into a job where everything was already fully established. There was always something launching, growing, or changing.

When I worked with Communion, they had just started their U.S. branch.
They were in a WeWork in the financial district in New York.

I was there while they were moving into their permanent office in Brooklyn, helping set things up, building contact databases, helping with their showcase series, managing street teams, all that stuff.

Then when I went back to school, I became their Philly rep and helped run their shows there.

It was really cool because there was so much to do, and I wasn’t just filling a role that ten people had already done before.

I was helping build things for the first time.
I sold merch, I promoted shows, I met artists, I did all kinds of stuff.

And I knew from working with Eva that I wanted to work at an agency.

I remember I kept trying to move to Chicago.
I wanted to work at The Windish Agency so bad.

I kept applying for openings there, and I got a call one day that said,
“We don’t have anything in Chicago, but we have a desk in San Diego.”

And I was like… I guess San Diego.

It was random, but it turned out I was working for one of the most badass female agents out there, so I was like,
“Oh, okay, cool. I’ll go do that.”

Mike: That’s amazing.

Was there anything about the job — either during internships or when you started full-time — that surprised you?
Something you didn’t expect you’d have to deal with?

Jess: Oh yeah.
I definitely underestimated how intense it was.

The volume of work is no joke.
You are managing so many things at once.

What I liked about Paradigm — and I’m biased because that’s where I came up — is that it felt very entrepreneurial.

From what I understand, some agencies have more structure where assistants rotate desks and roles are very defined.

At Paradigm, it was more like,
“You are this agent’s assistant. Everything that comes through, you’re involved in.”

So my job didn’t look the same as someone else’s job, because our roster wasn’t the same.

We had Imagine Dragons doing arenas and stadiums, and we also had smaller developing artists.

We were very involved in the teams, so we were helping with a lot of different things, not just one task.

There’s endless work.

I always tell assistants now:
Your to-do list will never be done.

If you finish the day and think,
“Great, I did everything,”
you probably missed something.

Mike: Yeah, I can see that.

Jess: You have to change your mindset.

You’re never going to feel like everything is done.
You just have to feel like everything is under control.

You have to know that nothing urgent is being missed.

You learn to exist in chaos and manage it.

When people told me the job would be intense, I was like,
“Yeah, yeah, whatever, I can handle it.”

And I could, but it’s way more than you expect.

If someone tells you it’s intense, believe them —
and then prepare for it to be ten times more.

Mike: Speaking of expectations, I wanted to flip this a little bit to the client side.

Representing artists, I know how important it is to set expectations about what everyone’s role is.

From your experience, what are things you wish artists understood about what you did as an agent?

Jess: I think most artists know this, but I’ve seen dynamics that weren’t great.

For context, I was a festival agent, so I wasn’t managing long-term artist relationships the same way some agents do.
I liked working project-based — build the event, finish the event, move on.

But the best teams are the ones where everyone has a relationship with the artist.

Getting an agent doesn’t mean you made it.
That’s when the work starts.

You have to make sure the team is the right fit.
You have to listen to their experience, but also protect yourself.

My biggest advice to artists is:
Have a relationship with your agent.
Know your manager.
Know your label.
Know the assistant on your team.

I had artists who knew everyone on the team, and that meant so much.
Not just personally, but professionally.

You never know when a relationship might change, so having that connection matters.

At the same time, keep it professional.
It is business at the end of the day.

You might need to make a tough decision someday.
You might need a new agent.
You might need to change teams.

And you can’t feel like you’re betraying your best friend when that happens.

Everyone is making money off your career.
You have to protect it.

Mike: That makes a lot of sense. And it’s interesting too, because this industry is so relationship-based.
You never know when you’re going to cross paths with someone again, so the way you handle those situations really matters.

Jess: Totally.
It’s such a small industry.

You really can’t burn bridges if you can help it.
Even if something doesn’t work out, you want to leave things on good terms.

There are people I worked with early in my career who I still talk to now, and sometimes those are the people who end up helping you later, or you help them later.

It’s all connected.

Mike: So at this point you’re working at Paradigm, things are moving, you’re learning the business, you’re working with festivals…

Was there a moment where you started thinking,
“Okay, what’s next for me?”

Jess: Yeah, I think that feeling always comes back every few years.

You get to a point where you’ve learned a lot, you’re comfortable, and then you start asking yourself,
“Am I growing?
Am I building something?
Or am I just maintaining?”

And I think that’s a really important question to keep asking.

Because if you stop asking it, that’s when you get stuck.

For me, I realized that I liked building things more than I liked maintaining things.

I liked when something was new.
I liked when there was structure to figure out.
I liked when there was chaos that needed organization.

When things got too routine, I started to feel restless.

Mike: That’s interesting, because a lot of people want the opposite.
They want stability, they want routine, they want to know exactly what their job is every day.

Jess: Yeah, and there’s nothing wrong with that.
Some people thrive in that environment.

But I realized that I don’t.

I like when there’s a problem to solve.
I like when there’s something that doesn’t exist yet and we have to figure out how to make it work.

That’s why a lot of my career ended up being in situations where something new was happening.

Even when I left Paradigm, I went to Arrival, which was a newer company at the time.
Then that became part of Wasserman.

Again, it was change.
It was building.
It was figuring things out.

Mike: Was that a scary move at the time?

Jess: Yeah, of course.
Every move is scary.

Especially in the agency world, because you’re leaving relationships behind, you’re leaving security behind, and you don’t know exactly how things are going to go.

But I think if you’re not a little scared, it probably means you’re not challenging yourself.

And every time I made a move, it was because I felt like I needed to grow.

Mike: Then COVID hits.
And that changed everything for live events.

Jess: Yeah… that was wild.

Everything just stopped.

For people who work in live music, it was like the entire world disappeared overnight.

There was no touring, no festivals, no shows, nothing.

And I think that forced a lot of people to ask themselves what they actually wanted.

Because when the thing you’ve been working toward suddenly isn’t there anymore, you have to figure out who you are without it.

For me, that was a big turning point.

I realized that I didn’t just want to go back to doing the same thing the same way.

I wanted to build something that felt more balanced.
Something that felt more sustainable.

Mike: Is that when the idea for Root & Trellis started?

Jess: Yeah, kind of.

It wasn’t like I woke up one day and said,
“I’m going to start a company.”

It was more that people kept coming to me asking for help.

They’d say,
“Can you help us organize this?”
“Can you help us build this team?”
“Can you help us figure out our structure?”

And I realized that the thing I liked the most in my career was that part —
building systems, building teams, building infrastructure.

So eventually I thought,
Why don’t I just do this?

Instead of doing it inside someone else’s company, I can do it for multiple companies.

Mike: That’s such an interesting transition, because it’s not the obvious next step from being an agent.

Jess: Yeah, and honestly, I think a lot of people in the industry don’t even realize those kinds of jobs exist.

We think of the music industry as artists, managers, agents, labels…

But there’s also operations.
There’s strategy.
There’s infrastructure.

There are people whose job is to make sure everything actually works.

And that’s what I realized I liked the most.

I like making the machine run.

Mike: And now you’re doing that through Root & Trellis, but you’re also involved with Book More Women, which is another really important part of your work.

Can you talk about how that came into your life?

Jess: Yeah.

So Book More Women started as a spreadsheet.

Literally just a spreadsheet.

It was a list of women in the live music industry, because people kept saying,
“We can’t find women for these jobs.”

And the response was,
“They exist. Here they are.”

It grew from there into a community, and then into an organization.

I got involved because I believed in what they were doing, and because I had experienced a lot of the same things.

Working in live music as a woman, especially early on, you notice pretty quickly how male-dominated it is.

And it’s not always intentional, but the imbalance is real.

So being part of something that’s trying to fix that, even a little bit, felt important to me.

Mike: I love that, because it shows how something small can grow into something meaningful just by solving a real problem.

Jess: Exactly.
It wasn’t some big master plan.

It was just people saying,
“We can’t find women to hire.”

And the answer was,
“Yes you can. You just have to look.”

And once the list existed, people started using it.
Then more people wanted to be added to it.
Then it became a community.

And now it’s something that actually helps people get hired, helps people find each other, and helps make the industry a little more balanced.

Mike: That’s awesome.

So now with Root & Trellis, what exactly are you doing for companies?
Because I think a lot of people hear that and don’t fully understand what that kind of work looks like.

Jess: Yeah, it’s a weird job to explain.

Basically, I help companies build structure.

A lot of companies grow really fast, especially in music, events, or entertainment, and they don’t always have the infrastructure to support that growth.

They have great ideas.
They have great people.
But the systems aren’t there yet.

So I come in and help figure out things like:

How should this team be organized?
Who should be responsible for what?
How do we communicate better?
How do we make this sustainable?

Sometimes that means building processes.
Sometimes it means hiring the right people.
Sometimes it just means helping everyone get on the same page.

It’s not glamorous, but it’s really important.

Mike: Honestly, that’s the kind of work that keeps everything from falling apart.

Jess: Exactly.

And I like it because every project is different.
Every company has different problems.

It feels a lot like the agency world in that way, where you’re juggling a lot of things, but instead of selling shows, you’re building systems.

Mike: Looking back at your career, from interning, to agencies, to festivals, to starting your own company…

What advice would you give to someone who wants to work in the music industry now?

Jess: I would say a few things.

First, you have to really want it.
It’s not an easy industry.

There’s a lot of work, the hours can be long, the pay isn’t always great at the beginning, and you have to be okay with that for a while.

Second, keep checking in with yourself.

Make sure the sacrifice is worth it.
Make sure you’re still excited about what you’re doing.
Make sure you’re growing.

Because if you’re not, it’s okay to change direction.

And third, don’t burn bridges.

This industry is too small.
You will see the same people again and again.

Be professional.
Be kind.
Do good work.

That stuff really matters more than people think.

Mike: That’s great advice.

And I think that check-in idea is really important, because a lot of people get so focused on the goal that they forget to ask if the goal still makes sense.

Jess: Exactly.

You only have one life.

You can work really hard, and that’s okay, but make sure you know why you’re doing it.

Make sure the trade-off makes sense for you.

Mike: I love that.

Last question — and this is the question I ask everybody on the show.

If you could give one piece of advice to your younger self, what would it be?

Jess: I would say… trust that things will work out.

I think when you’re younger, you feel like every decision is permanent.
Like if you make the wrong move, everything is over.

And that’s not true.

You can change directions.
You can try something new.
You can leave a job.
You can start over.

Most people’s careers aren’t a straight line.

So I would tell my younger self to relax a little bit, keep working hard, and trust that if you stay curious and keep putting in effort, things will end up where they’re supposed to.

Mike: That’s perfect.

Jess, thank you so much for being on the show.
This was awesome.

Jess: Thank you for having me. This was great.