Episode 301: From 40 Guitar Students to Two Thriving Businesses: How Rachel Lipson Built Multiple Income Streams Without Burning Out
You Know That Friend Who Just Has It Together?
Rachel Lipson is that friend. Except when you sit down and actually talk to her, you realize she doesn't have it all together. She's just figured out how to follow what lights her up and trust the process.
She started as a preschool teacher who needed extra cash. So she waitressed. She babysat. She played guitar gigs at night. When she'd babysit, she'd bring her guitar along because she had a show later. The kids loved it. Parents noticed.
"Would you teach my child guitar?"
That one question changed everything.
Today, Rachel's building multiple businesses: Blue Balloon Songwriting for Small People (a music education company) and Brooklyn Family Travelers (helping families travel the world using credit card points). She's been featured in the New York Times, Forbes, Bloomberg, and Condé Nast. Her first business? It runs without her now. Like, actually runs without her.
Sarah Walton, founder of Game On Girlfriend® podcast and business coach for women entrepreneurs, sat down with Rachel to get the real story. Not the highlight reel—the behind-the-scenes truth about building multiple businesses while staying sane.
She Didn't Plan to Start a Business—She Just Said Yes
Let's back up to where this actually started.
Rachel wasn't dreaming of being an entrepreneur. She was a preschool teacher who literally couldn't pay her bills on her salary alone. So she hustled. Nights, weekends, whenever she could squeeze in extra work.
The guitar thing? That was just convenience. She'd have it with her for gigs, so she'd play with the kids she babysat. Parents started asking if she'd teach their kids. She said yes. Those parents told other parents. Word-of-mouth did its thing.
By the time Rachel decided to leave her teaching job, she had 40 weekly private students. Forty. While working full-time.
When Everyone Said She'd Regret It
Here's where it gets interesting.
When Rachel told people at the preschool she was leaving, some of them warned her: "You're going to regret this. There's this amazing private school, and if you teach there, you'd be more likely to get your kids in."
Rachel didn't have kids yet. She had a boyfriend (now her husband). But the idea of staying in a job so her hypothetical future children could get into a private school? That didn't sit right.
"I was like, I don't think I can keep this job just for these hypothetical children I might have someday," she remembers.
So she quit. Went all-in on teaching music. Blue Balloon Songwriting was born
The Mistakes She Made (And Is Making Again)
Rachel will be the first to tell you—she made a lot of mistakes building Blue Balloon. The wild part? She's making some of the same ones with her second business.
"If I had a degree in business, I probably would not have launched a business. If I knew then what I know now, I would probably have been too scared to even take a leap." — Rachel Lipson
That's the truth of it, right? Sometimes, not knowing what you don't know gives you the courage to start.
Everything Lived in Her Head for Years
One of Rachel's biggest struggles? Getting her knowledge out of her head and into actual systems.
For years—years—everything about how Blue Balloon operated existed only in her brain.
"Everything was in my head. It took years to get it out of my head. Years," she says. "It took many people as a team to do the work I was doing just by myself. Not because they're not amazing employees. I had all these shortcuts. Mental shortcuts because I'd memorized everything."
She was basically doing the job of three people. Not because she was superhuman. Because she'd built all these workarounds that only made sense to her.
She Couldn't Let Go
Beyond the systems issue, Rachel really struggled with delegation.
"I took on too much all the time and had a really hard time bringing on people to help, hiring my weaknesses—all those things."
Sound familiar?
She believed what so many of us believe: no one else could do it as well as she could. "I thought that nobody could do the job I was doing. I thought I was the only one who could do it. That if I handed the reins to anybody else, the business would fold."
That mindset kept her working insane hours for years.
The Burnout That Actually Saved Her Business
Then COVID hit.
Like everyone else, Rachel was suddenly managing her business, homeschooling two young kids, and trying to keep her household from completely falling apart. No childcare. No backup. No grocery delivery slots.
"I really thought I could do it forever," Rachel reflects. "Then COVID hit. My kids were home. I needed to do all the things. Our house was a mess. We couldn't get groceries. It really made me realize—I couldn't do it forever."
Something had to give.
The Trip That Changed Everything
With her business coach's support, Rachel made a decision that terrified her.
She planned a family vacation and left her laptop at home. Not in her bag. Not "just in case." At. Home.
"I didn't bring my computer. Closed it and left it at home," she says. "We had a plan. If the team needed me, they'd reach out. If they couldn't reach me, they'd contact my husband."
For eight whole days, Rachel completely disconnected.
"My business did not fold in the eight days I was away. It actually was great and fine. I came back, and there were a couple things to handle. But overall, they had it down." — Rachel Lipson
Can we sit with that for a second?
The business she'd been convinced would collapse without her? It thrived.
She planned another trip. Then another. Eventually, she realized she'd actually built what so many of us dream of—a business that doesn't need her in the day-to-day.
When Free Advice Becomes Your Next Business
So now Rachel's traveling more with her family. Which is amazing, except for one small problem: "I'm going to run out of money because this is getting notable. These expenses add up."
She started figuring out creative ways to travel cheaper. Home swapping. Credit card points. Miles strategies. The more she learned, the more fascinated she became. And the more fascinated she became, the more people started asking her questions.
"I couldn't help it—once I started learning about it, people kept asking me about it," Rachel explains. "I'm spending day after day just fielding text messages and emails. People asking, 'Can I pick your brain on this? I'm planning a trip here. Which credit card should I get?"
Pay Attention to What People Keep Asking You For
Here's where Rachel had her lightbulb moment:
"Wait a minute. I'm spending all this time offering free advice. That's a really good indication that might be the next direction you want to go."
— Rachel Lipson
Boom. Brooklyn Family Travelers was born.
The platform helps families learn how to use credit card points to travel without going broke. Plus tons of practical tips for traveling with kids to places beyond all-inclusive resorts.
"It really is meeting them where they're at," Rachel says. "It's also like—what happens if you take your kids to Budapest? What if you take your kids to Morocco? There's so many ways people can travel. I try to make it feel more accessible."
Building Multiple Businesses: What's Different This Time
Here's what's wild.
Rachel admits she's making some of the same mistakes with Brooklyn Family Travelers that she made with Blue Balloon. But there's one huge difference.
She's Keeping It Just Her (On Purpose)
"One of the things I love about Brooklyn Family Travelers is that it's just me," Rachel says. "I have people I can bounce ideas off of. Collaborators and things like that. But I'm not responsible for managing anybody."
After 17 years of managing a team at Blue Balloon, Rachel wanted something different. "More of what I was doing was managing people and dealing with the bigger picture stuff. That isn't always fun. It isn't always creative."
With Brooklyn Family Travelers, she gets to be in creation mode. "I have an idea, and I just sit down and do it versus having to delegate. Even when delegating, there's still a level of explaining it to somebody. Hearing their feedback. Wondering if they think it's a good idea."
It's Not a Trap This Time—It's a Choice
This is the game-changer:
"This is so different from last time. Last time I did it, and it became its own trap. I thought I had to do it or it wouldn't sustain itself. Now I'm like, 'Oh, I'm still doing this, but it's by choice. I could choose to not do it this way. That's a really big difference. It feels very free."
— Rachel Lipson
She's doing the same thing (running everything herself). But this time she knows she doesn't have to. That awareness changes everything.
Let's Talk About the Work-Life Balance Myth
Rachel's refreshingly honest about what it's really like. Running two businesses while raising two kids (almost 10 and 12 now). Staying married. Traveling regularly.
"Some days I do it better than others. I am not perfect by any imagination," she admits. "In some ways, I live the dream. I'm doing what I always wished I could do. I'm living the life that's greater than what I could have ever dreamed for."
But Here's the Reality
"I'm always working. I don't really—I'm never really off. You're not clocking in. But you're also never clocking out."
Any entrepreneur reading this is probably nodding so hard their neck hurts, right?
Rachel's learned to watch for her own warning signs. "The last trip I took, I brought my computer. I was like, 'Oh, that's a sign. Don't do that again.'"
She Follows What Lights Her Up
Despite the challenges, Rachel's approach is simple. Follow what excites you instead of what looks good on paper.
"Right now I'm doing the things I really enjoy. I believe that if you lead with your passions and do the things you love, I've had this gift so far of being able to monetize that. It's contagious. People feel that. They're excited about it too."
Her Substack for Brooklyn Family Travelers? It's a bestseller with paid subscribers. Is it the most efficient use of her time from an ROI perspective? Maybe not. But she loves it, so she keeps doing it.
And honestly? That might be the whole secret.
The Lessons Rachel Learned (So You Don't Have To)
1. Your Side Hustle Is Trying to Tell You Something
Rachel didn't plan to build a business. She just said yes when parents asked her to teach guitar. Pay attention to what people keep asking you for. There's usually a business hiding in there.
2. Get It Out of Your Head (Seriously, Do It Now)
It took Rachel years to document her processes. Years.
Yes, it felt slower than just doing everything herself. But that investment? It gave her the freedom to actually step back.
"You have to look at those moments as an investment. Yes, you can do it faster as the founder. But if you spend your time training somebody, that's an investment in your business and in yourself. Now you've taken something off your plate."
— Rachel Lipson
3. Sometimes Burnout Is the Breakthrough
Rachel's biggest business breakthrough came from completely burning out during COVID-19 pandemic. Sometimes, the best thing you can do for your business? Step away from it.
4. Build the Business Your Life Needs Right Now
Blue Balloon forced Rachel to become a manager and a leader. Brooklyn Family Travelers lets her stay creative.
Both businesses are successful. But they serve different needs at different life stages.
There's no "right" way to do this. Just the way that works for you right now.
5. Know Your Warning Signs
Rachel knows that bringing her laptop on vacation means she's slipping back into old patterns. What are your warning signs? Identify them. Actually respect them.
What She Wishes She'd Known Sooner
When asked what she'd do differently, Rachel doesn't sugarcoat it:
"There's so many things I would have done differently. But I am also happy with how it unfolded. I think I learned a lot from the way I did things."
Her biggest regrets? "Things I wish I had done sooner—getting things out of my own head and bringing other people on."
But here's the twist. Her lack of business training might have actually helped. "If I had a degree in business, I probably would not have launched a business."
Sometimes, not knowing what you're "supposed" to do gives you permission to start.
The Thread That Connects Music and Travel
At first, Rachel worried. Running a music school for kids and a family travel company seemed random.
"It felt like a weird departure from what I had been doing. I was confused," she admits.
But once she got comfortable with it, she saw the connection.
It's All About Expanding What's Possible
"There really is this common thread of building community. Building creativity. Giving children, especially this opportunity to see the world," she explains.
Both businesses help kids (and their parents) see beyond their everyday bubble.
"Giving parents an opportunity to see the world through their kids' eyes. Giving kids an opportunity to see the world through other people's eyes—maybe outside of their bubble. That's a real gift. It is very similar to what songwriting does when you expose kids to it."
— Rachel Lipson
What Rachel Wants You to Know About Building Multiple Businesses
You Don't Have to Do It the Same Way Twice
Rachel intentionally built Brooklyn Family Travelers differently from Blue Balloon. After years of team management, she wanted to stay solo for a while.
"I am really enjoying being able to just have my business of me right now," she says. "Knowing that that's probably not going to last. I just can't help myself and will grow it."
Watch for the Patterns
Brooklyn Family Travelers exists because people wouldn't stop asking Rachel travel questions.
When you're constantly giving the same advice for free? That's usually your next business knocking.
Balance Looks Different at Every Stage
Rachel's kids are older now (almost 10 and 12). That changes everything about her capacity.
"They're not little anymore. My older son is like 5'2 and I'm tall. He's almost up there," she notes. Your version of balance will continue to shift. That's not failure. That's life.
Follow What You Love, Sort Out the Business Part Later
Rachel didn't start with market research and business plans. She followed her genuine interests. Songwriting. Music education. Travel. Helping families see the world.
"I'm doing the things I love with this feeling of—I believe that if you lead with your passions and do the things you love, you have this gift of being able to monetize that. It's contagious. People feel that. They're excited about it too."
The Real Talk About Self-Care
When Sarah asked Rachel about her self-care practices, her answer was so honest it hurt a little.
"I write songs. I play guitar. I love hanging out with my dog. I love to read. I love to listen to music. I love being home and making it feel like mine. Home design and aesthetics and all that."
Sounds pretty great, right?
"I would say that I don't spend enough time doing any of that stuff anymore. I know I waste so much time just scrolling. Mindlessly scrolling. Spending time on devices."
There it is.
Even successful multi-business owners struggle with the same stuff we all do.
"I really would love to spend more time reading and writing. Doing all the things I really love," Rachel admits. Her honesty makes her success feel more real, not less. You don't have to have everything perfectly balanced to build thriving businesses. You have to keep showing up.
Want to Connect with Rachel?
Blue Balloon Songwriting for Small People
Rachel offers in-home private music lessons mostly in New York City (with some availability in other cities). Plus virtual lessons everywhere. They work with kids and adults, including parents who want to learn alongside their kids, which is pretty special.
- Website: www.blueballoonschool.com
- Instagram: @blueballoonschool
Brooklyn Family Travelers
This is where Rachel helps families understand the concept of credit card points. So you can actually afford to travel with your kids. Plus tons of practical tips for family travel that go beyond resorts.
- Website: www.brooklynfamilytravelers.com
- Instagram: @bkfamilytravelers
- Substack: Brooklyn Family Travelers (free family travel tips and deep-dive guides)
Rachel's always happy to answer questions about credit cards and travel strategies. "I'm always happy to answer questions. Give people credit card advice. It's a big part of what I do. Offering strategies around which credit cards make sense to open. Which cards to keep, close, or use."
Here's What This Whole Conversation Is Really About
Rachel's story matters because it proves there's no single "right" path to building a successful business. No business degree. No formal business plan. No venture capital. No traditional startup playbook.
She just followed what felt necessary. Learned from her mistakes. Built systems when the pain of not having them finally outweighed the pain of creating them.
Her journey from preschool teacher to founder of two successful businesses was made possible because she paid attention. She noticed what people kept asking her for. She said yes to opportunities that aligned with her interests. She eventually learned to trust other people with what she'd built.
"You don't need to have everything figured out before you start. You don't need perfect systems before you launch. You don't need to scale in a specific way or follow someone else's timeline."
Sometimes the most successful businesses don't come from grand visions and detailed plans. They come from noticing what people keep asking you for help with. And having the courage to say yes.
About Rachel Lipson
An entrepreneur, songwriter, educator, points and miles expert, and avid family traveler, Rachel is the founder and CEO of two companies: Blue Balloon Songwriting for Small People (a songwriting school for kids) and Brooklyn Family Travelers, a platform dedicated to helping families travel meaningfully and affordably (mostly on credit card points!) with kids in tow.
Rachel has been featured dozens of times in various publications, including the New York Times, New York magazine, The New York Post, Time Out, Forbes, Bloomberg, Condé Nast, Inc., Success, and more. She has appeared on many podcasts and panels and has built multiple successful businesses in the fields of music, entrepreneurship, travel, and education.
Rachel lives in Park Slope, Brooklyn, with her husband, two kids, and a pup, and while she loves traveling the world, there is no place like home.
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About Sarah Walton
Sarah Walton is a business coach, podcast host, and mentor who helps women entrepreneurs build businesses they love. She's the creator of the Abundance Academy, Effortless Sales, and the Game On Girlfriend® podcast. Sarah's mission is to put more money in the hands of more women while teaching authentic, heart-centered business strategies.
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